Novel composition containing acyl group

ABSTRACT

According to the present invention, a process is provided for producing an acyl group-containing composition that includes a step of reacting a long chain N-acyl acidic amino acid anhydride with one or more compounds which have, per molecule, m functional groups of one kind or more selected from the group consisting of hydroxyl, amino and thiol groups in an aqueous solvent and/or a mixed solvent of water and an organic solvent (reaction step). The process makes it possible to produce an acyl group-containing composition that is free from coloration under moderate conditions.

TECHNICAL FIELD

The present invention relates to an acyl group-containing compositionthat comprises a long chain N-acyl acidic amino acid derivative and isof high purity and free from much coloration, and to a process foreasily producing the same which uses a long chain N-acyl acidic aminoacid anhydride.

BACKGROUND ART

There have been known various anionic surfactants useful as componentsof cleansing agents or cosmetics. It is known that surfactants have toexcel in surface activities such as detergency and forming properties.However, with the recent diversification of consumers' needs or anincrease in consumers' desire for high-quality articles, they are alsorequired not only to be less irritating to the skin, ophthalmic mucousmembrane or the like, but also to make products that are free fromcoloration or turbidity and give a more favorable feel to the skin. Inaddition, there is a growing tendency for consumers to require, from thestandpoint of burdening the environment, that surfactants have goodbiodegradability and exert a surface active effect even when used insmall amounts.

Traditionally, anionic surfactants such as alkyl sulfates,polyoxyethylene alkyl sulfates and alkyl benzene sulfonates have beenused. However, many of these surfactants are not satisfactory in thatthey strongly irritate the skin at the time of use. Anionic surfactantsthat are highly safe and excel in biodegradability are amino acidsurfactants such as, for example, long chain N-acyl amino-acid salts andderivatives thereof. These surfactants, however, are not satisfactorywith respect to surface activity at low concentrations, and thecoloration and turbidity of products containing them at lowtemperatures.

An example of a processes of the prior art for producing a long chainN-acyl acidic amino acid derivative is disclosed in JP-A-50-2973, inwhich an N-acyl amino acid menthol ester is obtained by dissolving, along chain N-acyl acidic amino acid anhydride and menthol in toluol orbenzol in the presence of p-toluenesulfonic acid as a catalyst at around100° C. for reaction, and then neutralizing, water-washing and dryingthe reaction product. In this process, however, coloration in theresultant long chain N-acyl acidic menthol ester (light-yellow) isinevitable because the reaction temperature is high also, industriallyimplementing the process is difficult because the process involvescomplicated operations such as neutralization, water washing and drying.

In JP-A-2000-44554, there is disclosed a process for producing asurfactant composed of a long chain N-acyl acidic amino acid derivative,in which a long chain N-acyl acidic amino acid anhydride is reacted witha compound having a hydroxyl group or an amino group, just like theprocess disclosed in JP-A-50-2973 described above. In this process, inorder to prevent coloration in the end product, the reaction is carriedout at temperatures higher than the melting point of any one of theingredients so that the ingredient is in the liquid state during thereaction, or the reaction is carried out in an inert solvent such astoluene while keeping any one of the ingredients in the liquid state.This process is, however, not a satisfactory one with respect topreventing coloration and the reaction yield (purity) of the endproduct.

For example, in JP-A-2000-44554, an embodiment is described in whichN-lauroylglutamic acid anhydride and a sugar, such as sorbitol, or anamino acid, such as L-glutamic acid, are reacted without a solvent at ahigh temperature of 100° C. or more. In this process, formation ofby-products is inevitable and coloration occurs in the product also, thereaction yield is too low to obtain the intended surfactant having highpurity. The specification describes that the reaction can be carried outusing an inert solvent such as toluene. However, when reactingN-lauroylglutamic acid anhydride and a sugar, such as sorbitol, or anamino acid, such as L-glutamic acid, the reaction has to be carried outat a high temperature of 100° C. or more so that the reaction is that oftwo phases, a solid phase and a liquid phase, since the solubility ofthese ingredients in a solvent is low. As a result, the process is not asatisfactory one with respect to the coloration and purity of the endproduct.

The present inventors have already disclosed in JP-A-2002-167313 an acylgroup-containing composition (surfactant) that contains a long chainN-acyl acidic amino acid derivative produced by reacting one or morecompounds which have, per molecule, m functional groups of one kind ormore selected from the group consisting of hydroxyl, amino and thiolgroups with a long chain N-acyl acidic amino acid anhydride, and aprocess for producing the same. The inventors have made sure that theresultant acyl group-containing composition has surface activity even atlow concentrations and does not practically irritate the skin. However,the acyl group-containing composition obtained by this process is notsatisfactory in that when it is neutralized and takes the form of anaqueous solution, significant coloration or turbidity occurs and itsstability is not good. Further, the reaction yield of the composition isnot satisfactorily high, and due to the high impurity content, theresultant composition has to be chromatographed to enhance the endproduct's purity.

In this reaction process, the reaction is also carried out attemperatures higher than the melting point of any one of the ingredientsor by using an inert solvent, just like the process disclosed inJP-A-2000-44554 described above. Accordingly, when reacting a long chainN-acyl acidic amino acid anhydride with an amino acid in an inertsolvent such as toluene, since an amino acid is hard to dissolve insolvents other than water, the reaction temperature has to be elevatedto allow the reaction to procede. As a result, by-products areinevitably formed due to the secondary reaction characteristic of thereaction, which causes coloration or turbidity in the end product.

Further, acyl compounds as the reaction products do not highly dissolvein a solvent, either, or have a high melting point. Therefore, in areaction without a solvent or in an organic solvent, they can sometimesprecipitate as intermediate products in the course of the reaction. Dueto the necessity to prevent such a situation, the reaction temperaturehas to be set at around 100° C. or higher.

The present inventors have found that (i) one of the by-products formedin such reactions (reactions carried out at temperatures equal to orhigher than the melting point of any one of the ingredients used or byusing an inert solvent, just as disclosed in JP-A-2002 -167313 andJP-A-2000-44554) has a molecular weight smaller than that of the acylcompound as the intended end product of the reactions by 18 and (ii) theby-product is hard to remove even by separating operations such asseparation by chromatography. In fact, such a by-product could not beremoved in a separation by chromatography conducted in the examples ofthe process disclosed in JP-A-2002-167313 and was a cause of colorationin the resultant acyl compound.

Thus, the drawbacks of the prior art lead to a first demand, that is, anacyl group-containing composition, as an anionic surfactant which isless irritating to the skin or the like and has a satisfactory surfaceactivity even at low concentrations, and which contains a long chainN-acyl acidic amino acid derivative, wherein the composition contains asmaller amount of by-products, thereby being free from coloration andturbidity when it takes the form of an aqueous solution, and can be moreeasily produced in a high yield.

In the meantime, there are various kinds of gelatinous compositions,which are prepared by mixing an oil ingredient with an aqueous solventand allowing the mixture to take the form of a gel. The term “gel” usedherein means a form of compositions which contain liquid over a widecontent range, such as a paste, a cream or a jelly, as described in TheBasis of Colloid Chemistry, Dainippon Tosho, 1976: 245. For example,JP-A-55-141243 discloses an oily gelatinous composition which isprepared by using sodium stearate as a gelling agent and fat and oil asa mediator. The gelatinous composition thus prepared is not satisfactoryin that its gel strength is not enough, and cracks are likely to occurin the composition. Moreover, because its hardness is fixed, it does nothave arbitrary hardness.

JP-A-55-81655 discloses a gelatinous aromatic substance in which awater-soluble polymer compound, as a gelling agent, is generally addedto make the composition gel. However, gelatinous compositions obtainedby this process are not satisfactory in that when they are left attemperatures of around 40 to 50° C., their oil ingredients tend toseparate or the polymerization degree of the polymers added tends tochange which increases or decreases the viscosity of the compositions,and thus their stability deteriorates with time.

Examples of cosmetics which use gelatinous compositions includegelatinous cleansing agents. Such gelatinous cleansing agents areprepared, for example, by mixing an oil ingredient with an aqueoussolvent and allowing the mixture to take the form of a gel. Then awater-soluble polymer compound known as a gelling agent is commonlyadded. When using a gelatinous composition formed with a water-solublepolymer compound for cleansing cosmetics, the resultant cleansingcosmetics are not satisfactory in that they do not spread well, theirdetergency is questionable and they are sticky even after washing withwater. Moreover, their stability deteriorates with time as describedabove.

Meanwhile, there exists an oil gel which is obtained by making oil togel with a gelling agent. However, the use of an oil gel makes it hardto adjust the viscosity of gelatinous compositions produced from it.Moreover, when using it for a cleansing agent such as a makeup remover,it cannot be washed from the skin with water, and it needs to be wipedoff with tissue paper or the like after use and then cleaned off againwith a facial cleanser, etc. There also exist gelatinous compositionswhich are water-in-oil emulsions. Also in this case, the oil phase is acontinuous phase, and thus when using the compositions for cleansingagents, they need to be cleaned off the skin again with a facialcleanser, etc., just like the case of an oil gel. In either case, thehands become sticky with the oil ingredients, and the cleansing agentdoes not have a favorable feel.

Gelatinous compositions which are oil-in-water emulsions are also known.These types of compositions can be washed from the skin with waterwithout a wipe-off operation as described above. However, their oilingredients often remain on the skin and cannot be washed off completelyfrom the skin using only water. Further, they have a poor compatibilitywith oily pollutants and their cleansing performance is notsatisfactory. Thus, many compositions of this type have been examinedwhile changing the kind or amount of the oil ingredient or surfactantused. However, there no compositions have been provided that aresatisfactory in terms of stability and pleasant feel on the skin.

JP-A-10-219278 discloses compositions of anionic surfactants containingtwo long-chain acyl groups and two polar groups. The specificationstates that the compositions can take the form of a gel or a paste ifdesired; however, it discloses only aqueous solutions of thecompositions as cleansing agents and does not describe the gelatinousoil compositions at all.

Thus, the above described drawbacks of the prior art led to a seconddemand, that is, a gelatinous composition which contains oil ingredientsin a stable manner and can have arbitrary hardness in a range of thehardness of a paste to that of a solid, thereby overcoming the abovedescribed drawbacks.

Traditionally, cosmetics such as creams, milks and lotions have beenallowed to contain a relatively large amount of moisturizing agents suchas various types of oil ingredients or glycerol so as to leave the skinfeeling moist or give the skin a sufficient moisturizing effect aftertheir application. However, trying to leave the skin feeling furthermoist or giving the skin a better moisturizing effect often results inleaving the skin feeling excessively oily or sticky or makes theemulsified system unstable, which causes its separation with time, andhence the product deterioration. On the contrary, increasing the contentof a surfactant so as to improve the stability of the emulsified systemoften results in increasing the irritation to the skin. Thus, it hasbeen difficult to satisfy, at the same time, the moist feeling on theskin or the skin moisturizing effect of the composition, the betterfeeling on the skin after the application of the composition, and thestability of the products of the composition.

JP-A-10-203956 discloses cosmetics which contain a polyhydric alcoholand an amide compound having a specified structure, that excel in skinmoisturizing effects, and will not feel sticky on the skin. However, thestability of its emulsified state is not fully satisfied.

JP-A-10-218754 discloses cosmetics composed of an anionic surfactantcontaining two long-chain acyl groups and two polar groups, powderand/or fine powder, and water. However, the cosmetics are notsatisfactory with respect to stability, etc., though they feel better atthe time of their application and have an improved skin moisturizingeffect.

Thus, the above described drawbacks of the prior art led to a thirddemand, that is, cosmetics which excel not only in having a moistfeeling on the a skin and a skin moisturizing effect, but also in beingstable in an emulsified state.

There has been a tendency in recent years to use pigments, instead ofdyes, as colorants for aqueous compositions for use in writingimplements, recording instruments, printers or liquid cosmetics. This isbecause pigment colorants are superior in water resistance and lightresistance. However, unlike dyes, pigments are insoluble or hardlysoluble in water, and therefore it is necessary to disperse pigmentsstably in water. As dispersants used for this purpose, various types ofnonionic or anionic surfactants, cellulose derivatives, or water-solublepolymers such as nonionic polymers have been used independently or inthe form of a mixture. However, the method described above cannotdisperse pigments well and is insufficient to cope with the occurrenceof sedimentation or aggregation with time.

In oil makeup cosmetics, etc., it is generally necessary to disperse aninorganic pigment such as talc, mica, titanium dioxide or kaolin in anoil base material. However, such inorganic pigments are highlyhydrophilic, and thus they do not disperse well in an oil base material,which causes problems such as deterioration of product quality.

For example, titanium dioxide is used in cosmetics to screen the skinfrom ultraviolet rays. The screening effect is produced when theparticles of titanium dioxide are in a finely dispersed state.Accordingly, if the particles are not dispersed well and aggregate, theeffect becomes insufficient. In delivery apparatuses for writingimplements, recording instruments, printers or liquid cosmetics,sedimentation of pigments may cause problems such as clogging of thedelivery portions.

JP-A-10-218754 discloses cosmetics composed of an anionic surfactantcontaining two long-chain acyl groups and two polar groups, powderand/or fine powder, and water. However, the cosmetics are notsatisfactory yet in respect to stability, etc., though they feel betterat the time of their application and have improved moisturizing effect.

Generally, the affinity of dispersants varies depending on whether thepigment is hydrophilic or hydrophobic, and therefore the effectivenessof the dispersion also varies. As a result, there has been no dispersantcomposition which has satisfactory dispersion stability to hydrophilicpigment and/or hydrophobic pigment.

Thus, the above described drawbacks of the prior art led to a fourthdemand, that is, a dispersant composition which has a high dispersionstability with respect to hydrophilic powder and/or hydrophobic powder.

DISCLOSURE OF THE INVENTION

As is apparent from the above description of “Background Art,” an objectof this invention is to provide an acyl group-containing composition, asan anionic surfactant that is less irritating to the skin or the likeand has a sufficient surface activity even at low concentrations, whichcontains a long chain N-acyl acidic amino acid derivative and forms asmaller amount of by-products, and therefore, does not cause colorationor turbidity when it takes the form of an aqueous solution, and to aprocess for easily producing the above described composition in a highyield.

Another object of this invention is to provide a gelatinous compositionthat contains oil ingredients in a stable manner and can have arbitraryhardness in the range of the hardness of a paste to that of a solid.

Another object of this invention is to provide cosmetics which excel notonly in having a moist feeling on the skin and a skin moisturizingeffect, but also in being stable in an emulsified state.

Still another object of this invention is to provide a dispersantcomposition which has a high dispersion stability with respect tohydrophilic powder and/or hydrophobic powder.

After directing tremendous research efforts toward the above describedproblems, the present inventors have ascertained that in the acylgroup-containing compositions produced by conventional processes, thereexists a reaction by-product, which is a characteristic of thecompositions, besides the acyl compound as the intended end product.Thus they have found that (a) such a by-product is formed when acondensation reaction is carried out between a long chain N-acyl acidicamino acid anhydride and one or more compounds which have a hydroxyl,thiol or amino group without a solvent or with a non-aqueous solvent, asdescribed in the documents of the prior art; (b) the tendency toward theby-product formation grows with an increase in the reaction temperature;and (c) the larger the amount of the by-product contained in the acylgroup-containing composition, the higher the degree of coloration orturbidity caused in the composition when in the form of an aqueoussolution. Mass spectrometry of the by-product has shown that themolecular weight of the by-product is smaller than that of the acylcompound, as the intended product, by 18. This leads to the presumptionthat the by-product is the acyl compound after it has undergonedehydration (one molecule of H₂O). Thus the by-product is defined hereinas a “dehydrated acyl compound.”

The inventors tried to remove the dehydrated acyl compound from the acylgroup-containing composition. Their attempt using, for example,chromatographic treatment increased the purity of the acyl compound to aconsiderable extent, but could not remove the dehydrated acyl compound.In other words, the method using chromatographic treatment can removeby-products other than the dehydrated acyl compound, but can hardlyremove the dehydrated acyl compound. The reason that the dehydrated acylcompound is hard to separate by chromatographic treatment is probablybecause the polarity of the acyl compound and that of the dehydratedacyl compound are very close to each other.

So then, the inventors examined whether the formation of the dehydratedacyl compound itself can be retarded or not. Surprisingly, theexamination revealed that in the process for producing the acylgroup-containing composition of this invention in which a long chainN-acyl acidic amino acid anhydride is reacted with a compound having mfunctional groups of one kind or more selected from the group consistingof hydroxyl, amino and thiol groups, when the reaction was carried outin a water-based solvent (aqueous solvent and/or mixed solvent of waterand an organic solvent), which is usually active to anhydrides, theformation of the above described dehydrated acyl compound could besignificantly retarded. In other words, the reaction solution obtainedthrough the above described reaction was already colorless and clearbefore carrying out a by-product removing operation.

Also surprisingly, the inventors have found that in the reaction processin a water-based medium, though the reaction uses an anhydride, an acylgroup-containing composition as an object substance can be produced atlow temperatures very effectively and in a very high yield, comparedwith conventional reactions carried out in an inert solvent. Employing areaction process in which the reaction is carried out in an aqueousmedium enables the production of an acyl group-containing compositionfree from coloration and of high purity without conducting achromatographic treatment after the reaction. Under conventionalreaction conditions, in which no solvent or a non-aqueous solvent isused, the purity of the acyl group-containing composition in thereaction product is no more than about 60% by weight. On the other hand,under reaction conditions in which an aqueous medium is used, an acylgroup-containing composition with purity of 90% by weight or more can beeasily obtained (this depends on other factors, though). The productionprocess of this invention has overcome the problems of the prior artjust by using a water-based solvent as a reaction solvent and hasfurther advanced the purity of the product in a very easy and simpleway. This is a remarkable technological improvement in terms ofindustrial implementation.

Further, unexpectedly, the inventors have also found the followingeffects. In the production process of this invention, since the reactionis carried out in a water-based solvent, N-acyl acidic amino acidanhydride inevitably undergoes hydrolysis, and a very small amount of along chain N-acyl acidic amino acid or a salt thereof remains in theacyl group-containing composition. The very small amount of the longchain N-acyl acidic amino acid or the salt thereof remaining in the acylgroup-containing composition lowers the Krafft point of the acylgroup-containing composition and improves the stability, formingproperties, lather creaminess, texture, feelings such as the feeling atthe time of washing and a refreshing feeling, and the thickeningperformance of a cleanser comprising an aqueous solution of thecomposition.

The present inventors also directed their research efforts towardspecifying the characteristics of the acyl group-containing compositionof this invention and have found several advantages thereof. They haveascertained, as one of the advantages, that the use of the acylgroup-containing composition of this invention makes it possible toprovide a gelatinous composition that contains oil ingredients in astable manner and in a gelatinous state without a gelling agent, excelsin stability with time, and can have arbitrary hardness in the range ofthe hardness of a paste to that of a solid. Surprisingly, the gelatinouscomposition obtained as above extremely excels in its dispersibility inwater. Thus, the inventors have found that the gelatinous composition isa useful composition as a base material for cleansing agents, etc. whichcan be easily washed with water after application to the skin, do notremain on the skin after application and have an excellent afterfeel andthat the gelatinous composition having a viscosity in a certain rangehas excellent spreading characteristics when applied on the skin or thelike. They have also found that the appearance of the gelatinouscomposition is so transparent that the difference in the index ofrefraction between the water phase that is composed of a surfactant, apolyhydroxyl compound and water and the oil phase composed of oilingredients is small.

They have ascertained, as a second advantage of the characteristics ofthe acyl group-containing composition of this invention, that cosmeticscontaining a specified amount of the acyl group-containing compositionexcel not only in providing a moist feeling on the skin and a skinmoisturizing effect, but also in their stability in an emulsified state.They have also found that a very stable milky lotion can be produced byusing an oil gelatinous composition composed of one kind or more acylgroup-containing compositions of this invention, one or morepolyhydroxyl compounds having 2 or more hydroxyl groups per molecule andone or more oil ingredients.

Further, the inventors have found a third advantage of thecharacteristics of the acyl group-containing composition of thisinvention, that is, the acyl group-containing composition has a highdispersion stability with respect to hydrophilic powder and/orhydrophobic powder.

Specifically, the present invention is made up as follows.

-   [1] A method of producing an acyl group-containing composition    comprising a step of reacting a long chain N-acyl acidic amino acid    anhydride represented by the following formula (1):    [Formula 1]    wherein R¹CO represents a long chain acyl group derived from a    saturated or unsaturated fatty acid with 2 to 20 carbon atoms; R² is    hydrogen or a lower alkyl group with 1 to 3 carbon atoms which is    optionally substituted with a hydroxyl or carboxyl group; j, k are    independently any of 0, 1 and 2 and are not 0 at the same time, with    one or more compounds having, per molecule, m functional groups of    one kind or more selected from the group consisting of hydroxyl,    amino and thiol groups in an aqueous solvent and/or a mixed solvent    of water and an organic solvent, which is defined as reaction step,    -   wherein the acyl group-containing composition comprises at least        one acyl compound represented by the following general formula        (2):        [Formula 2]        wherein R¹CO, R², and j, k each represent the same as those        defined in the above formula (1); n (n is an integer of 2 to 20,        including 2 and 20) Zs are bonding portions to which m (m≧n)        functional groups of one kind or more selected from the group        consisting of hydroxyl, amino and thiol groups substituted on X        bind and which are selected independently from the group        consisting of —O—, —NR³— (R³ is hydrogen, or an alkyl, an        alkenyl, an aryl or an alkylaryl group with 1 to 10 carbon        atoms) and —S—; X is a spacer of a straight, branched or cyclic        hydrocarbon chain of molecular weight of 1,000,000 or less which        optionally has substituents other than hydroxyl, amino and thiol        groups and contains or does not contain an aromatic hydrocarbon;        n substituents represented by the following general formula (3):        [Formula 3]        wherein reference characters each represent the same as those        defined in the above formula (2),        which are attached to X via Z are independent of each other; and        Y represents a carboxyl group or the salt thereof.-   [2] The method according to the above description [1], wherein in    the general formula (2), X is a spacer of a straight, branched or    cyclic hydrocarbon chain with 1 to 40 carbon atoms which optionally    has substituents other than hydroxyl, amino and thiol groups and    contains or does not contain an aromatic hydrocarbon.-   [3] The method according to the above description [1] or [2],    wherein in said reaction step, the molar ratio of the total of the    functional groups contained in the one or more compounds having, per    molecule, m functional groups of one kind or more selected from the    group consisting of hydroxyl, amino and thiol groups to the long    chain N-acyl acidic amino acid anhydride represented by the    formula (1) is 0.5 to 1.4 and the pH of the reaction solution is    kept at 4 to 14 at the time of reaction.-   [4] The method according to any one of the above descriptions [1] to    [3], further comprising, as step(s) carried out after said reaction    step, either one or both of (i) a step of separating the reaction    solution derived from said reaction step into two layers, an organic    layer and a water layer, by adjusting the pH of the reaction    solution to 1 to 6 using a mineral acid to obtain an organic layer    which contains the acyl group-containing composition, which is    defined as an acid-precipitation and layer-separation step and (ii)    a step of separating, at 35° C. to 80° C., the mixture of the acyl    group-containing composition, which contains water-soluble    impurities such as inorganic salts, and the medium, which    substantially contains water and tertiary butanol as main    ingredients, into a water layer and an organic layer containing the    acyl group-containing composition to remove impurities in the acyl    group-containing composition, which is defined as a washing step.-   [5] The method according to any one of the above descriptions [1] to    [4], wherein after said reaction step, or after said    acid-precipitation and layer-separation step or washing step, the    organic solvent is distilled off from the organic layer, which    contains the acyl group-containing composition, using a spray    evaporator in which a mixed solution is allowed to take the form of    a vapor-liquid mixed phase and is sprayed within the evaporator to    evaporate the solvent.-   [6] An acyl group-containing composition comprising at least one    acyl compound represented by the following formula (2):    [Formula 2]    wherein R¹CO represents a long chain acyl group derived from a    saturated or unsaturated fatty acid with 2 to 20 carbon atoms; R² is    hydrogen or a lower alkyl group with 1 to 3 carbon atoms which is    optionally substituted with a hydroxyl or carboxyl group; j, k are    independently any of 0, 1 and 2 and are not 0 at the same time; n (n    is an integer of 2 to 20, including 2 and 20) Zs are bonding    portions to which m (m≧n) functional groups of one kind or more    selected from the group consisting of hydroxyl, amino and thiol    groups substituted on X bind and which are selected independently    from the group consisting of —O—, —NR³— (R³ is hydrogen, or an    alkyl, an alkenyl, an aryl or an alkylaryl group with 1 to 10 carbon    atoms) and —S—; X is a spacer of a straight, branched or cyclic    hydrocarbon chain of molecular weight of 1,000,000 or less which    optionally has substituents other than hydroxyl, amino and thiol    groups and contains or does not contain an aromatic hydrocarbon; n    substituents represented by the following general formula (3):    [Formula 3]    wherein reference characters each represent the same as those    defined in the above formula (2), which are attached to X via Z are    independent of each other; and Y represents a carboxyl group or the    salt thereof, wherein the content of the acyl compound in the    composition is 70% by weight or more, the content of free fatty acid    is 3% by weight or less, and the content of a compound whose    molecular weight is smaller than that of the acyl compound by 18 is    5% or less in terms of its area ratio to the acyl compound which is    obtained by the analysis of liquid chromatography using a detector    at 205 nm.-   [7] The composition according to the above description [6],    comprising 0.5 to 30% by weight of a long chain N-acyl acidic amino    acid or a salt thereof.-   [8] The composition according to the above description [6] or [7],    wherein in the general formula (2), X is a spacer of a straight,    branched or cyclic hydrocarbon chain with 1 to 40 carbon atoms which    optionally has substituents other than hydroxyl, amino and thiol    groups and contains or does not contain an aromatic hydrocarbon.-   [9] The composition according to any one of the above descriptions    [6] to [8], wherein in the general formula (2), R¹CO is a long chain    acyl group derived from a saturated or unsaturated fatty acid with 8    to 20 carbon atoms.-   [10] The composition according to any one of the above descriptions    [6] to [9], wherein in the general formula (2), X has at least one    group independently selected from the group consisting of carboxyl,    sulfonic acid, sulfate ester and phosphate ester groups and the    salts thereof.-   [11] The composition according to any one of the above descriptions    [6] to [10], comprising 0.2 to 1.5 equivalent of basic substance, as    a counter ion, per 1 equivalent of dissociated groups in said acyl    group-containing compound.-   [12] The composition according to any one of the above descriptions    [6] to [11], wherein the transmittances at 430 nm and 550 nm are    both 90% or more when said acyl group-containing composition is    formed into an aqueous solution having a solids content of 20% by    weight and a pH of 10.-   [13] The composition according to the above description [10] or    [11], further comprising other surfactant (s).-   [14] The composition according to any one of the above descriptions    [6] to [13], comprising at least one acyl compound represented by    the general formula (2) which is produced through a step of reacting    a long chain N-acyl acidic amino acid anhydride represented by the    following formula (1):    [Formula 1]    wherein reference characters represent the same as those defined    above, with one or more compounds having, per molecule, m functional    groups of one kind or more selected from the group consisting of    hydroxyl, amino and thiol groups in water and/or a mixed solvent of    water and an organic solvent, which is defined as reaction step.-   [15] The composition according to the above description [14],    wherein the one or more compounds having, per molecule, m functional    groups of one kind or more selected from the group consisting of    hydroxyl, amino and thiol groups independently have, per molecule,    at least one group, other than hydroxyl, amino and thiol groups,    selected from the group consisting of carboxyl, sulfonic acid,    sulfate ester and phosphate ester groups and the salts thereof.-   [16] The composition according to descriptions [14] or [15], wherein    the composition is produced by carrying out, after said reaction    step, either one or both of (i) a step of separating the reaction    solution derived from said reaction step into two layers, an organic    layer and a water layer, by adjusting the pH of the reaction    solution to 1 to 6 using a mineral acid to obtain an organic layer    containing the acyl group-containing composition, which is defined    as an acid-precipitation and layer-separation step and (ii) a step    of separating, at 35° C. to 80° C., the mixture of the acyl    group-containing composition, which contains water-soluble    impurities such as inorganic salts, and the medium, which    substantially contains water and tertiary butanol as main    ingredients, into a water layer and an organic layer containing the    acyl group-containing composition to remove impurities in the acyl    group-containing composition, which is defined as a washing step.-   [17] The composition according to any one of the above descriptions    [14] to [16], wherein the composition is produced by distilling off    the organic solvent, after said reaction step, or after said    acid-precipitation and layer-separation step or washing step, from    the organic layer which contains the acyl group-containing    composition using a spray evaporator in which a mixed solution is    allowed to take the form of a vapor-liquid mixed phase and is    sprayed within the evaporator to evaporate the solvent.-   [18] A composition in the form of a liquid, a solid, a gel, a paste    or a mist, comprising one or more of the acyl group-comprising    compositions according to any one of the above descriptions [6] to    [17].-   [19] A cosmetic composition in the form of a liquid, a solid, a gel,    a paste or a mist, comprising one or more of the acyl    group-containing compositions according to any one of the above    descriptions [6] to [17].-   [20] The cosmetic composition according to the above description    [19], further comprising one or more polyhydroxyl compounds.-   [21] The cosmetic composition according to the above description    [20], wherein the content of polyhydroxyl compounds in the above    described cosmetic composition is 0.1 to 60% by weight and the    weight ratio of the content of the acyl group-containing    compositions to the content of the polyhydroxyl compounds in said    cosmetic composition is 10/1 to 1/100.-   [22] The cosmetic composition according to the above description    [20] or [21], further comprising one or more oil ingredients and    being in the form of a gel.-   [23] A gelatinous composition comprising one kind or more of the    acyl group-containing compositions according to any one of the above    descriptions [6] to [17], one or more polyhydroxyl compounds and one    or more oil ingredients, wherein the water content in the gelatinous    composition is 50% by weight or less and the composition of the    gelatinous composition is such that 1) the total amount of the acyl    group-containing compositions is 0.1 to 40% by weight, 2) the total    amount of the polyhydroxyl compounds is 1 to 60% by weight, and 3)    the total amount of the oil ingredients is 1 to 95% by weight.-   [24] The gelatinous composition according to the above description    [23], wherein the difference in refractive index at 20° C. between    the water layer containing the acyl group-containing composition(s),    the polyhydroxyl compound(s) and water, and the oil layer containing    the oil ingredients, in the gelatinous composition is +0.05 or less.-   [25] The gelatinous composition according to the above description    [23] or [24], wherein its viscosity at 25° C. is 1,000 to 200,000    mPa·s.    [26] Use of the gelatinous composition according to any one of the    above descriptions [23] to [25] for cleansing agents.-   [27] A cosmetic composition, prepared by emulsifying the gelatinous    composition according to any one of the above descriptions [23] to    [25].-   [28] A dispersant composition which comprises one or more of the    acyl group-containing compositions according to any one of the above    descriptions [6] to [17] and is in the form of a liquid, a solid, a    gel, a paste or a mist.

BEST MODE FOR CARRYING OUT THE INVENTION

In the following the present invention will be described in detailparticularly in terms of its embodiments.

The acyl group-containing composition according to this inventioncontains an acyl compound having, per molecule, more than one acyl groupas a hydrophobic group and more than one hydrophilic group, asrepresented by the general formula (2).

The acyl groups represented by R¹CO in the general formula (2) areindependent of each other. In other words, they may be different or thesame. They may be any acyl groups as long as they are derived from asaturated or unsaturated fatty acid with 2 to 20 carbon atoms. It doesnot matter whether they are straight-chain, branched-chain orcyclic-chain acyl groups.

Examples of R¹CO include acyl groups derived from the following acids:straight-chain fatty acids such as acetic acid, propionic acid, butyricacid, pentanoic acid, hexanoic acid, heptanioc acid, caprylic acid,pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoicacid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid,stearic acid, nonadecanoic acid and arachic acid; branched-chain fattyacids such as 2-butyl-5-methylpentanoic acid,2-isobutyl-5-methylpentanoic acid, dimethyloctanoic acid,dimethylnonanoic acid, 2-butyl-5-methylhexanoic acid, methylundecanoicacid, dimethyldecanoic acid, 2-ethyl-3-methylnonanoic acid,2,2-dimethyl-4-ethyloctanoic acid, methyldocosanoic acid,2-propyl-3-methylnonanoic acid, methyltridecanoic acid,dimethyldodecanoic acid, 2-butyl-3-methylnonanoic acid,methyltetradecanoic acid, ethyltridecanoic acid, propyldodecanoic acid,butylundecanoic acid, pentyldecanoic acid, hexylnonanoic acid,2-(3-methylbutyl)-3-methylnonanoic acid,2-(2-methylbutyl)-3-methylnonanoic acid, butylethylnonanoic acid,methylpentadecanoic acid, ethyltetradecanoic acid, propyltridecanoicacid, butyldodecanoic acid, pentylundecanoic acid, hexyldecanoic acid,heptylnonanoic acid, dimethyltetradecanoic acid, butylpentylheptanoicacid, trimethyltridecanoic acid, methylhexadecanoic acid,ethylpentadecanoic acid, propyltetradecanoic acid, butyltridecanoicacid, pentyldodecanoic acid, hexylundecanoic acid, heptyldecanoic acid,methylheptylnonanoic acid, dipentylheptanoic acid, methylheptadecanoicacid, ethylhexadecanoic acid, ethylhexadecanoic acid,propylpentadecanoic acid, butyltetradecanoic acid, pentyltridecanoicacid, hexyldodecanoic acid, heptylundecanoic acid, octyldecanoic acid,dimethylhexadecanoic acid, methyloctylnonanoic acid, methyloctadecanoicacid, ethylheptadecanoic acid, dimethylheptadecanoic acid,methyloctyldecanoic acid, methylnonadecanoic acid, methylnonadecanoicacid, dimethyloctadecanoic acid and butylheptylnonanoic acid;straight-chain monoen acids such as octene acid, nonene acid, deceneacid, caprolenic acid, undecylenic acid, linderic acid, obtusilic acid,lauroleinic acid, tridecene acid, tsuzuic acid, myristoleic acid,pentadecene acid, hexedecene acid, palmitoleic acid, heptadecene acid,octadecene acid, oleic acid, nonadecene acid and gondoic acid; branchedmonoene acids such as methylheptene acid, methylnonene acid,methylundecene acid, dimethyldecene acid, methyldodecene acid,methyltridecene acid, dimethyldodecene acid, dimethyltridecene acid,methyloctadecene acid, dimethylheptadecene acid and ethyloctadeceneacid; di- or tri-ene acids such as linoleic acid, linoelaidic acid,eleostearic acid, linolenic acid, linolenelaidic acid, pseudoeleostearicacid, parinaric acid and arachidonic acid; acetylenic acids such asoctynoic acid, nonynoic acid, decynoic acid, undecynoic acid, dodecynoicacid, tridecynoic acid, tetradecynoic acid, pentadecynoic acid,heptadecynoic acid octadecynoic acid, nonadecynoic acid anddimethyloctadecynoic acid; and cyclic acids such asmethyleneoctadecenoic acid, methyleneoctdecanoic acid, aleprolic acid,aleprestic acid, aleprylic acid, alepric acid, hydonocarpic acid,chaulmoogric acid, gorlic acid, α-cyclopentyl acid, α-cyclohexyl acidand α-cyclopentylethyl acid.

R¹CO may be acyl groups derived from fatty acids obtained from naturalfats and oils, as long as they are derived from mixed fatty acids whichcontain 80% or more of the above described saturated or unsaturatedfatty acids with 2 to 20 carbon atoms. Examples of such acyl groupsinclude acyl groups derived from, for example, coconut oil fatty acid,palm oil fatty acid, linseed oil fatty acid, sunflower oil fatty acid,soybean oil fatty acid, sesame oil fatty acid, castor oil fatty acid,olive oil fatty acid, camellia oil fatty acid, rapeseed oil fatty acidand palm stone oil fatty acid.

The kind of the R¹CO can be selected depending on the purpose for whichthey are used, since surface activity varies depending on the kind ofthe R¹CO. When using the composition as a surfactant, preferably R¹COwith 8 to 20 carbon atoms are selected.

In the general formula (2), R² represents a hydrogen atom or a loweralkyl group with 1 to 3 carbon atoms which is optionally substitutedwith a hydroxyl, carboxyl, sulfonic acid, sulfate ester or phosphateester group, or a salt thereof. Examples of such lower alkyl groupsinclude methyl, ethyl, propyl, isopropyl, hydroxymethyl, hydroxyethyl,hydroxyl(iso)propyl, dihydroxy(iso)propyl, carboxymethyl, carboxyethyl,carbpxypropyl and sulfoethyl groups.

In the general formula (2), n substituents (formula (3)) attached to Xare independent of each other. In other words, they may be different orthe same. The formula (3) represents, what is called, N-acylated acidicamino acid, and it does not matter which optically isomericconfiguration each substituent has. It may be a D-isomer, L-isomer orracemate.

The acidic amino acid is a monoaminodicarboxylic acid having 2 carboxylgroups and one amino group per molecule. The amino group may be aN-methyl group or a N-ethyl group. It does not matter which opticallyisomeric configuration the acidic amino acid has. It may be a D-isomer,L-isomer or racemate. Examples of an acidic amino acid include gulutamicacid, asparagic acid, lanthionine, β-methyllanthionine, cystathionine,dienecholic acid, felinine, aminomalonic acid, β-oxyasparagic acid,α-amino-α-methylsuccinic acid, β-oxygulutamic acid, γ-oxygulutamic acid,γ-methylgulutamic acid, γ-methylenegulutamic acid,γ-methyl-γ-oxygulutamic acid, α-aminoadipic acid, α-amino-γ-oxyadipicacid, α-aminopimelic acid, α-amino-γ-oxypimelic acid, β-aminopimelicacid, α-aminosuberic acid, α-aminosebacic acid and pantothenic acid.

Preferably, n substituents (general formula (3)) attached to X areN-acylated L-acidic amino acid molecules, because such substituentsallow the acyl group-containing composition of this invention to excelin biodegradability.

In the general formula (2), n Zs attached to X are bonding portions(—O—, —NR³— and —S—) resulting from m (m≧n) functional groups (hydroxyl,amino or thiol groups) substituted on X bind. They are independent ofeach other. In other words, they may be different or the same. R³ ishydrogen, or an alkyl, an alkenyl, an aryl or an alkylaryl group with 1to 10 carbon atoms. Preferably, n Zs attached to X are bonding portions(—NR³—) resulting from amino groups substituted on X.

In the general formula (2), X is a spacer of a straight, a branched or acyclic hydrocarbon chain having a molecular weight of 1,000,000 or lesswhich has m functional groups of one kind or more selected from thegroup consisting of hydroxyl, amino and thiol groups and contains ordoes not contain an aromatic hydrocarbon. X may have substituents otherthan said hydroxyl, amino and thiol groups.

In the general formula (2), preferably X is an m-valent compound residuewhich has a molecular weight of 1,000,000 or less and has m functionalgroups of one kind or more selected from the group consisting ofhydroxyl, amino and thiol groups and X is compound residue which mayhave substituents other than hydroxyl, amino and thiol groups. Them-valent compound described above means a compound capable of forminglinkages resulting from m functional groups. It does not matter whichoptically isomeric configuration the compound has. It may be a D-isomer,L-isomer or racemate.

Examples of such m-valent compounds include: amino acids such as serine,threonine, cysteine, cystine, cystinedisulfoxide, cystathionine,methionine, arginine, lysine, tyrosine, histidine, tryptophan andoxyproline; compounds having, per molecule, an amino group(s) and ahydroxyl group(s) such as aminoethanol, aminopropanol, aminobutanol,aminopentanol, aminohexanol, aminopropanediol, aminoethylethanolamine,aminoethylaminoethanol, aminocresol, aminonaphthol,aminonaphtholsulfonic acid, aminohydroxybenzoic acid,aminohydroxydibutanioc acid, aminophenol, aminophenethyl alcohol andglucosamine; compounds having, per molecule, a thiol group and ahydroxyl group(s) such as mercaptoethanol, mercaptphenol,mercaptpropanediol and glucothiose; and compounds having, per molecule,a thiol group and an amino group such as aminothiophenol andaminotriazolethiol. The m-valent compounds may be proteins, peptides orthe hydrolyzed products thereof.

In the general formula (2), preferably X is an m-valent (m≧n)polyhydroxyl compound residue of molecular weight of 1,000,000 or lesswhich optionally has substituents other than a hydroxyl group. Them-valent polyhydroxyl compound herein means a compound capable offorming m ester linkages. It does not matter which optically isomericconfiguration the compound has. It may be a D-isomer, L-isomer orracemate.

Examples of m-valent polyhydroxyl compounds include: divalent hydroxylcompounds such as ethylene glycol, 1,2-propanediol, 1,3-propanediol,1,2-butanediol, 1,3-butanediol, 1,4-butanediol, pentanediol,1,6-hexanediol, cyclohexanediol, dimethylolcyclohexane, neopentylglycol, 1,8-octanediol, 2,2,4-trimethyl-1,3-pentanediol, isopreneglycol, 3-methyl-1,5-pentanediol, sorbite, catechol, resorcin,hydroquinone, bisphenol A, bisphenol F, hydrogenated bisphenol A,hydrogenated bisphenol F, dimerdiol, dimethylolpropionic acid,dimethylolbutanoic acid, tartaric acid, dihydroxytataric acid, mevalonicacid, 3,4-dihydroxycinnamic acid, 3,4-dihydroxyhydrocinnamic acid,hydroxybenzoic acid, dihydroxystearic acid, dihydroxyphenylalanine andthe isomers thereof; trivalent polyhydroxyl compounds such as glycerol,trioxyisobutane, 1,2,3-butanetriol, 1,2,3-pentanetriol,2-methyl-1,2,3-propanetriol, 2-methyl-2,3,4-butanetriol,2-ethyl-1,2,3-butanetriol, 2,3,4-pentanetriol, 2,3,4-hexanetriol,4-propyl-3,4,5-heptanetriol, 2,4-dimethyl-2,3,4-petanetriol,1,2,4-butanetriol, 1,2,4-pentanetriol, trimethylolethane,trimethylolpropane, diethanolamine, triethanolamine, trihydroxystearicacid; tetravalent polyhydroxyl compounds such as pentaerythritol,erythritol, 1,2,3,4-pentanetetrol, 2,3,4,5-hexanetetrol,1,2,4,5-pentanetetrol, 1,3,4,5-hexanetetrol, diglycerol and sorbitan;pentavalent polyhydroxyl compounds such as adonitol, arabitol, xylitoland triglycerol; hexavalent polyhydroxyl compounds such asdipentaerythritol, sorbitol, mannitol, iditol, inositol, dalsitol,talose and allose; and the dehydration condensation products thereof.

Examples of m-valent polyhydroxyl compounds include saccharides: forexample, monosaccharides, such as tetrose such as erythrose, threose anderythrulose, pentose such as ribose, arabinose, xylose, lyxose, xyluloseand ribulose, hexose such as allose, altrose, glucose, mannose, gulose,idose, galactose, tarose, fructose, sorbose, psicose and tagatose; andoligosaccharides such as maltose, isomaltose, cellobiose, gentiobiose,meribiose, lactose, turanose, treharose, saccharose, mannitriose,cellotriose, gentianose, raffinose, melezitose, cellotetrose andstachyose.

M-valent polyhydroxyl compounds may be other saccharide residues such asheptose, deoxy-saccharides, amino-saccharides, thio-saccharides,seleno-saccharides, aldonic saccharides, uronic acid, sugar acid,ketaldonic acid, anhydrosugars, unsaturated sugars, sugar esters, sugarethers and glycoside, or polysaccharides such as starch, glycogen,cellulose, chitin and chitosan, or hydrolyzed products thereof.

In the general formula (2), preferably X is an m-valent polyaminocompound residue of molecular weight of 1,000,000 or less whichoptionally has substituents other than an amino group. The m-valentpolyamino compound herein means a compound capable of forming m acidamido linkages. It does not matter which optically isomericconfiguration the compound has. It may be a D-isomer, L-isomer orracemate.

Examples of m-valent polyamino compounds include: aliphatic diaminessuch as N,N′-dimethylhydrazine, ethylenediamine,N,N′-dimethylethylenediamine, diaminopropane, diaminobutane,diaminopentane, diaminohexane, diaminoheptane, diaminooctane,diaminononane, diaminodecane, diaminododecane, diaminoadipic acid,diaminopropanoic acid, diaminobutanoic acid and the isomers thereof;aliphatic triamines such as diethylenetriamine, triaminohexane,triaminododecane, 1,8-diamino-4-aminomethyl-octane, 2,6-diaminocapricacid-2-aminoethyl ester, 1,3,6-triaminohexane, 1,6,11-triaminoundecane,di(aminoethyl)amine and the isomers thereof; alicyclic polyamines suchas diaminocyclobutane, diaminocyclohexane,3-aminomethyl-3,5,5-trimethylcyclohexylamine and triaminocyclohexane;aromatic polyamines such as diaminobenzene, diaminotoluene,diaminobenzoic acid, diaminoanthraquinone, diaminobenzenesulfonic acid,diaminobenzoic acid and the isomers thereof; aliphatic-aromaticpolyamines such as diaminoxylene, di(aminomethyl)benzene,di(aminomethyl)pyridine, di(aminomethyl)naphthalene and the isomersthereof; and hydroxyl group-substituted polyamines such asdiaminohydroxypropane and the isomers thereof.

In the general formula (2), preferably X is an m-valent polythiolcompound residue of molecular weight of 1,000,000 or less whichoptionally has substituents other than a thiol group. The m-valentpolythiol compound herein means a compound capable of forming mthioester linkages. It does not matter which optically isomericconfiguration the compound has. It may be a D-isomer, L-isomer orracemate.

Examples of m-valent polythiol compounds include dithiol compounds suchas dithioethylene glycol, dithioerythritol and dithiothreitol.

Of the above described compound residues, residues with 1 to 40 carbonatoms are preferable as X and those with 1 to 20 carbon atoms are morepreferable.

Preferably X contains, as substituents, at least one carboxyl group,sulfonic acid group, sulfate ester group, phosphate ester group or thesalts thereof independently, because with such X, the acylgroup-containing composition of this invention excels in solubility inweak-acid solution. Preferably X is in the naturally occurring form,because with such X, the acyl group-containing composition of thisinvention excels in biodegradability.

In the general formula (2), the carboxyl group represented by Y and thecarboxyl group(s), sulfonic acid group(s), sulfate ester group(s) orphosphate ester group(s) contained in X are capable of forming saltswith various basic substances.

Examples of such salts include alkaline metal salts, alkaline earthmetal salts, ammonium salts, organic amine salts and basic amino acidsalts. Concrete examples are salts of one or more basic substancesselected from the group consisting of alkaline metals such as sodium,potassium and lithium, alkaline earth metals such as calcium andmagnesium, metals such as aluminum and zinc, organic amines such asammonia, monoethanolamine, diethanolamine, triethanolamine andtriisopropanolamine, and basic amino acids such as arginine and lysine.Of these salts, sodium salts, potassium salts, organic amine salts andbasic amino acid salts are preferable.

Now, a method for producing an acyl group-containing composition of thisinvention will be described. The method includes a step of reacting along chain N-acyl acidic amino acid anhydride and a compound-having, permolecule, m functional groups of one kind or more selected from thegroup consisting of hydroxyl, amino and thiol groups in water and/or amixed solvent of water and an organic solvent.

The present inventors have found that the above described reaction stepproduces the following effects. First, even if amino acids orsaccharides, which are compounds slightly soluble in solvents other thanwater, are used as ingredients, such ingredients, and besides, acylcompounds as products can be dissolved in the reaction solvent underreaction conditions of around room temperature or lower, and thereforethe reaction solution can be kept in a uniform state until the reactionis completed. Thus, the reaction is allowed to progress under moderateconditions, which retards the formation of by-products, resulting in theproduction of an acyl group-containing composition of high purity.Particularly the amount of dehydrated acyl compound, a by-product whichconventional processes cannot avoid, can be restricted to a very smallamount.

A second effect is as follows. Since the production method of thisinvention uses a water-based solvent as a reaction solvent, thereremains in the acyl group-containing composition a long chain N-acylacidic amino acid or a salt thereof, which is produced by the inevitablehydrolysis of N-acyl acidic amino acid anhydride during the reaction.The inventors have found that this small amount of a long chain N-acylacidic amino acid or a salt thereof remaining in the acylgroup-containing composition produces unexpected effects. Specifically,the acyl group-containing composition of this invention is free fromcoloration, and besides, its following properties are improved due tothe presence of the long chain N-acyl acidic amino acid or the saltthereof.

-   -   Lowers the Krafft point of the acyl group-containing        composition, thereby improving its utility at low temperatures.    -   Increases the solubility of the acyl group-containing        composition in water, thereby make possible its use in a wider        and lower pH range (particularly in the weak-acid range).    -   Improves the stability of cleansing agents composed of the        aqueous solution of the acyl group-containing composition.    -   Improves the forming properties of cleansing agents composed of        the aqueous solution of the acyl group-containing composition        and the creaminess of the lather.    -   Makes finer the lather texture of cleansing agents composed of        the aqueous solution of the acyl group-containing composition.    -   Improves the touch of cleansing agents composed of the aqueous        solution of the acyl group-containing composition at the time of        washing.    -   Improves the feeling of refreshment users are given after        cleansing using cleansing agents composed of the aqueous        solution of the acyl group-containing composition.    -   Improves the thickening properties of an aqueous solution of the        acyl group-containing composition with a thickening agent.

From the viewpoint of the above described properties, preferably theacyl group-containing composition contains 0.5 to 30% by weight of along chain N-acyl acidic amino acid or the salt thereof, more preferably1 to 15% by weight and much more preferably 1 to 10% by weight.

A long chain N-acyl acidic amino acid anhydride represented by thegeneral formula (1) and used in this invention is an acidic amino acidhaving been acylated by a saturated or unsaturated fatty acid residuewith 2 to 20 carbon atoms which may be straight-, branched- orcyclic-chain. The amino group of the amino acid may be eitherN-methylated one or N-ethylated one. It does not matter which opticallyisomeric configuration the amino acid has. It may be a D-isomer,L-isomer or racemate.

Examples of such amino acids include a long chain N-acylglutamic acid,asparagic acid, lanthionine, β-methyllanthionine, cyctathionine,diencholic acid, felinine, aminomalonic acid, β-oxyasparagic acid,α-amino-α-methylsuccinic acid, β-oxyglutamic acid, γ-oxyglutamic acid,γ-methylglutamic acid, 7-methyleneglutamic acid, γ-methyl-γ-oxyglutamicacid, α-aminoadipic acid, α-amino-γ-oxyadipic acid, α-aminopimelic acid,α-amino-γ-oxypimelic acid, β-aminopimelic acid, α-aminosuberic acid,α-aminosebacic acid and pantothenic acid. Of these acidic amino acids,L-acidic amino acids are preferable, because when using them, theresultant acyl group-containing composition of this invention excels inbiodegradability.

Long chain N-acyl acidic amino acid anhydrides can be obtained easily bycommonly used synthetic methods. For example, even crude crystals of along chain N-acyl acidic amino acid anhydride obtained by reacting acarboxylic acid anhydride such as acetic anhydride with a long chainN-acyl acidic amino acid and then subjecting the reaction solution tocrystal precipitation, filtration and drying can be directly applied tothis invention.

The reaction step in the production method of this invention can becarried out by, for example, mixing a compound having m functionalgroups of one kind or more, which are selected from the group consistingof hydroxyl, thiol and amino groups, and a long chain N-acyl acidicamino acid anhydride, while stirring, in an aqueous solvent or a mixedsolvent of water and an organic solvent(s) (a single kind of or amixture of more than one kind of organic solvent). The important pointis that the compound having m functional groups of one kind or moreselected from the group consisting of hydroxyl, amino and thiol groupsis dissolved in the reaction solvent under the reaction conditions.

When reacting an amino acid or saccharide with a long chain N-acylacidic amino acid anhydride by a conventional process, the ingredientshave to be reacted in such a state that they are dispersed in asolution, because there is no appropriate solvent. Accordingly, severereaction conditions, for example, elevated reaction temperatures have tobe employed. On the other hand, in the method of this invention wherethe reaction medium is a water-based one, reaction can be carried outunder very moderate conditions. And the moderate reaction conditionsallow the formation of by-products to be restrained to a minimum.

The mixing ratio of water and an organic solvent applicable is in therange of 100/0 to 1/99 (volume ratio) and preferably 100/0 to 20/80(volume ratio). The state of such a mixed solvent may be a uniform phaseor non-uniform phase such as 2-phase as long as no precipitation occurs.

Examples of organic solvent applicable include tetrahydrofuran, benzene,toluene, xylene, carbon tetrachloride, chloroform, acetone, methyl ethylketone, cyclohexane, dioxane and tertiary butanol. The organic solventused in the production method of this invention need not be of highpurity, and it may be a water-containing organic solvent produced as,for example, water azeotrope. Organic solvents recovered from a reactionpurification system can also be used without purification.

In the reaction step of the production method of this invention, thereaction temperature is not particularly limited; however, generally,lower reaction temperatures are advantageous, because the lower thereaction temperature becomes, the smaller the formation rate of thehydrolyzed product of a long chain N-acyl acidic amino acid anhydridebecomes. However, too low a temperature may cause an increase inviscosity of the reaction solution or a setting of the same, whichresults in an impossibility of mixing or a significant decrease inreaction rate. Thus, a reaction temperature should be selected from atemperature range that permits such situations to be avoided. Thereaction temperature may be changed with time. Normally, the reactiontemperature is in the range of −5 to 100° C., preferably in the range of0 to 60° C. and more preferably in the range of 5 to 40° C.

In the reaction step of the production method of this invention, theconcentration of each ingredient prepared is not particularly limited.However, the concentration should be such that it allows the operationof mixing under stirring to be carried out during the reaction.Preferably the concentration is 0.1 to 50% by weight in terms of solidsconcentration.

In the reaction step of the production method of this invention,preferably the reaction is carried out while keeping the pH of thereaction solution in the range of 4 to 14. Alkaline substances used foradjusting the pH of the reaction solution include: for example,inorganic bases such as sodium hydroxide, potassium hydroxide, calciumhydroxide, barium hydroxide; and organic bases such as ammonia andorganic ammonium. Preferably, an aqueous solution of an inorganic baseis used.

If the pH of the reaction solution is lower than 4, by-products due tothe hydrolysis of a long chain N-acyl acidic amino acid anhydride areincreased, whereas if the pH is higher than 14, a larger amount ofalkaline substance than needed is consumed, and therefore the amount ofacid consumed in the next step is also increased, though no substantialdisadvantages occur. Thus, from the viewpoint of resource consumption,it is preferable to keep the pH of the reaction solution in the range of4 to 14, more preferably in the range of 6 to 13 and much morepreferably in the range of 9 to 12.

In the reaction step of the production method of this invention, thereaction can be carried out in the following manner. Specifically, itcan be carried out in a batchwise operation in which first, all of theprescribed amount of ingredients: one or more compounds selected fromthe compounds each having a hydroxyl, thiol or amino group; a solvent;and a long chain N-acyl acidic amino acid anhydride are prepared in astirring vessel, and then an alkaline substance is fed to the mixedsolution to keep the pH of the solution in a specified range. Or it canbe carried out in a semi-batch operation in which first, one kind ormore compounds having m functional groups of one kind or more, which areselected from the group consisting of hydroxyl, thiol and amino groupsand a solvent are prepared, and then a long chain N-acyl acidic aminoacid anhydride are continuously fed to form the mixed solution whilefeeding an alkaline substance to keep the pH of the solution in aprescribed range. Or it can be carried out in a continuous feedingoperation in which first a reaction solvent is prepared, and then one ormore compounds selected from the compounds each having a hydroxyl, thiolor amino group and a long chain N-acyl acidic amino acid anhydride arecontinuously fed at the same time. The reaction solution in the stirringvessel in which a prescribed amount of ingredients have been reacted canbe provided for the next step, that is, the acid-precipitation andlayer-separation step. When feeding a long chain N-acyl acidic aminoacid anhydride into the stirring vessel, the anhydride may be in theform of a powder or a solid, or in the form of a solution of the powderor the solid in an inert organic solvent capable of dissolving the sameor in the form of a slurry of the powder or solid dispersed in an inertorganic solvent.

A compound having m functional groups of one kind or more, which areselected from the group consisting of hydroxyl, thiol and amino groupswhich are used in the reaction step of the production method of thisinvention are compounds that have a straight-chain, branched-chain orcyclic-chain hydrocarbon chain of molecular weight of 1,000,000 or less,which contains or does not contain an aromatic hydrocarbon, andoptionally have substituents other than hydroxyl, thiol and aminogroups. As such compounds, compounds having a compound residue such asthe above described X can be used. The compound having m functionalgroups of one kind or more, which are selected from the groupsconsisting of hydroxyl, thiol and amino groups is preferably a compoundwith 1 to 40 carbon atoms. It is preferable that such compoundsindependently have, per molecule, at least one carboxyl group, sulfonicacid group, sulfate ester group, phosphate ester group or a saltthereof, as a substituent(s) other than hydroxyl, thiol and aminogroups, because with such compounds, the acyl group-containingcomposition of this invention excels in solubility in a weak-acidsolution.

In the reaction step of the production method of this invention, usuallypreferably the molar ratio of the total functional groups contained inone kind or more compounds having, per molecule, m functional groups ofone kind or more selected from the group consisting of hydroxyl, aminoand thiol groups to a long chain N-acyl acidic amino acid anhydride is0.1 to 5. To produce an acyl group-containing composition of high puritywith the least possible separation and purification treatment after thereaction, it is preferable to carry out the reaction in the molar ratiorange of 0.5 to 2, though its depends on the purpose for which the acylgroup-containing composition of this invention is used. If the molarratio is less than 0.5, the anhydride shows more tendency towardshydrolysis, which leads to an increase in the ratio of the long chainN-acyl acidic amino acid formation. On the other hand, if the molarratio is higher than 2, the amount of the compounds having a hydroxyl,thiol or amino group that remain unreacted tends to be increased, andsuch impurities require separation and purification treatment dependingon the purpose for which the acyl group-containing composition of thisinvention is used. The molar ratio is more preferably in the range of0.6 to 1.4 and much more preferably 0.75 to 1.15.

When employing the acid-precipitation and layer-separation step in theproduction method of this invention, the pH of the reaction solutionobtained in the above described reaction step is adjusted to 1 to 6 byadding a mineral acid such as hydrochloric acid or sulfuric acid to thesolution, thereby separating the reaction solution into two layers, anorganic layer and a water layer, allowing to obtain the organic layer,which includes an acyl group containing composition. In the reactionsolution, part of or all of the acyl group-containing composition formedexists in the form of an alkaline salt. Addition of a mineral acidallows part of or all of the carboxyl groups in the acylgroup-containing composition to be free acid, thereby separating thereaction solution into an organic layer and a water layer. In thisprocess, inorganic salts, which are water-soluble impurities, andunreacted compounds each having a hydroxyl, thiol or amino group move tothe water layer, thereby being removed from the acyl group-containingcomposition.

In the acid-precipitation and layer-separation step, it does not matterwhether an organic solvent is present or not. However, the presence ofan organic solvent makes the layer separation more likely to occur, andtherefore it is preferable to carry out the step in the presence of anorganic solvent. For example, when the reaction in the reaction step iscarried out with an aqueous solvent alone, an organic solvent is addedin the acid-precipitation and layer-separation step. Although thecontent of the organic solvent at the time of the acid-precipitation andlayer-separation may be determined arbitrarily, the content in the mixedsolution is preferably 0.01 to 99% by weight.

When using an organic solvent in the above described reaction step, theorganic solvent may be used at the time of the acid-precipitation andlayer-separation as well. Other organic solvents such as methanol,ethanol, propanol, isopropanol, butanol and isobutanol may also be used.Two kinds or more of these solvents can be used in combination. In thefollowing, the acid-precipitation and layer-separation step will bedescribed in detail in terms of a system where tertiary butanol alone isused as a preferable hydrophilic organic solvent.

The dissociation state of carboxyl group changes depending on the pH ofthe reaction solution at the time of acid-precipitation andlayer-separation. And the state of layer-separation, in other words, theweight ratio of the organic layer to the water layer or the removabilityof inorganic salts, changes a little with the change of the dissociationstate of carboxyl group. Accordingly, preferably the reaction is carriedout in the pH range of 1 to 3 and more preferably in the pH range of 1to 2.5.

The temperature at the time of acid-precipitation and layer-separationis preferably in the range of 35° C. to the boiling point of thehydrophilic organic solvent used. For example, when the hydrophilicorganic solvent is tertiary butanol, preferably the temperature is inthe range of 35° C. to 80° C. and more preferably in the range of 40° C.to 70° C. The reason of this is that if the temperature is lower than35° C., it takes a longer time for the system to attain layer-separationequilibrium. Or even if the system attains layer-separation equilibrium,a considerable amount of inorganic salts can sometimes remain in theorganic layer, or layer separation cannot sometimes occur depending onthe types of the acyl group-containing composition or its concentrationin the reaction solution. On the other hand, a temperature higher than80° C. is also disadvantageous, because if the temperature is higherthan 80° C., boiling is more likely to occur since the boiling point ofthe azeotropic composition of water/tertiary butanol is near 80° C. at anormal pressure.

When employing a washing step in the production method of thisinvention, the washing step, which is mainly intended to removeimpurities the acid-precipitation and layer-separation step cannotremove, may be carried out without the acid-precipitation andlayer-separation step. Specifically, the acyl group-containingcomposition, tertiary butanol and water are mixed so as to give acomposition which can be separated into two layers, an organic layer anda water layer, and then water-soluble impurities, mainly inorganic saltsor unreacted compounds each having a hydroxyl, thiol or amino group, inthe organic layer which includes the acyl group-containing compositionare moved to the water layer by solvent extraction. Just like the abovedescribed acid-precipitation and layer-separation step, the step will bedescribed in detail in terms of a system where tertiary butanol alone isused as a hydrophilic organic solvent.

The present inventors have found that a mixed solution of an acylgroup-containing composition of this invention/tertiary butanol/water isseparated into two layers, an organic layer that contains the acylgroup-containing composition, and a water layer, if only the compositionof the mixed solution is adjusted so that it falls in a specified range.They have also found that the above layer separation makes it possibleto remove the inorganic salts or unreacted compounds, each having ahydroxyl, thiol or amino group, in the organic layer. Specifically, ifwater and/or tertiary butanol is added to the organic phase formed inthe acid precipitation and layer separation step so as to give acomposition in which layer separation occurs, or tertiary butanol and/orwater is added to the acyl group-containing composition that contains alarge amount of impurities such as inorganic salts, layer separationoccurs in the system, thereby making it possible to remove the inorganicsalts etc, in the organic layer.

In both the acid-precipitation and layer-separation step and the washingstep, the higher the tertiary butanol concentration of the layerseparation region becomes, the shorter the time required for the layerseparation of the system becomes. Accordingly, it is preferable toincrease the concentration of tertiary butanol within the concentrationrange that permits layer separation. When employing the washing step,the washing temperature is 35 to 80° C. and preferably 40 to 70° C. forthe same reasons having been described in terms of theacid-precipitation and layer-separation step.

To take out the acyl group-containing composition from the organic layerafter layer separation, which contains only a decreased amount ofwater-soluble impurities such as inorganic salts, the organic solvent isremoved from the organic layer by fractional distillation or bycrystallization of the organic layer by acidification and cooling,followed by filtration.

The fractional distillation of the organic solvent may be carried out inaccordance with conventional procedures using a stirring vessel, or itmay be carried out using a thin film evaporator, such as a falling filmevaporator, centrifugal thin film evaporator or agitated thin filmevaporator, or using a spray evaporator. When removing the organicsolvent by fractional distillation, the part of the carboxyl groups inthe acyl group-containing composition may be neutralized or may not beneutralized before distilling off the solvent. However, the fractionaldistillation which involves neutralization of part of the carboxylgroups in the acyl group-containing composition is preferable in thatonce the organic solvent is removed, a neutralized aqueous solution ofthe acyl group-containing composition can be obtained directly.

Since solutions including an acyl group-containing composition arefoamable, it is not easy to carry out distillation efficiently on anindustrial scale while inhibiting the foaming of solutions. In thisrespect, distillation using a spray evaporator can be carried outefficiently even on an industrial scale. From that point of view, theprocess using a spray evaporator is preferable.

The distillation with a spray evaporator is to evaporate a solventusing, for example, an apparatus disclosed in JP-B-7-51201 in thefollowing steps: draining a solution from the bottom of an evaporatorcan; circulating the solution to a heat exchanger by using a pump tooverheat it to a prescribed extent; spraying the overheated solution inthe inside of the can through piping provided on the top of the can.This method has the following characteristics: (1) in the gas phaseportion of the evaporator can, one or more nearly cylindrical tube tipis provided with its end facing the solution surface and is connected tothe piping provided on the top of the can; (2) the overheated solutionhaving been passed through the heat exchanger is evaporated, until itreaches the tube tip, by controlling the flow rate of the solution inthe heat exchanger and the overheated degree of the same at the outletof the heat exchanger to obtain a gas-liquid two-phase flow; and (3) theamount of the overheat remaining in the solution droplets having beensprayed through the tube tip is released in the gas phase portion untilthe droplets reach the surface of the liquid phase in the evaporationcan.

This method enables the production of an acyl group-containingcomposition of considerably low degree of coloration and of high purity.

The acyl compounds represented by the general formula (2) can beisolated from the acyl group-containing composition produced by theabove described methods by properly adopting purification means known inthe art.

The acyl group-containing composition of this invention contains an acylcompound at a purity of 70% by weight or more. If the purity is low, theefficiency of the composition as a surfactant is decreased, or thedesired physical properties of the acyl group-containing composition ofthis invention can sometimes be impaired. Further preferably, the purityof the acyl compound is 85% by weight or more.

The acyl group-containing composition of this invention contains only atrace amount of dehydrated acyl compound product derived from an acylcompound, and preferably the content is 5% or less in terms of its arearatio to the acyl compound which is obtained by the analysis by highperformance liquid chromatography using a detector at 205 nm. Thedehydrated acyl compound is very hard to separate from the acylcompound, and once the dehydrated acyl compound is formed, it is verydifficult to remove it completely by purification. When the acylgroup-containing composition is used in the form of an aqueous solution,the lower the content of the dehydrated acyl compound, the less theturbidity or coloration of the aqueous solution. Thus, the content ispreferably 3% or less and more preferably 1% or less (based on the abovedescribed analytical method).

The acyl group-containing composition of this invention can beneutralized by a basic substance, and therefore it can be used asaqueous solutions having a wide pH region if its neutralization rate isadjusted. Preferably, the acyl group-containing composition is used insuch a state that 0.2 to 2 equivalent of 1 equivalent of its dissociatedgroup (carboxyl group) is neutralized (i.e., neutralization rate is 0.2to 2).

Preferably, the acyl group-containing composition of this invention issuch that when it is neutralized with, for example, sodium hydroxide andprepared into a 20% by weight aqueous solution of pH 10, thetransmittances both at 430 nm and at 550 nm are 90% or more. Sinceoccurrence of turbidity or coloration in its aqueous solution lowers itsvalue as a commercial product, it is preferable that either one of thetransmittances is 90% or more and more preferably 95% or more.

The acyl group-containing composition of this invention can be useddirectly as a surfactant depending on the application for which thesurfactant is used and can also be used in the form of an aqueoussolution. The composition can sometimes be hard to handle as a solid atordinary temperature depending on its properties. In such a case,preferably it is handled in the form of an aqueous solution. Forexample, aqueous solutions containing the acyl group-containingcomposition can have a pH ranging from 3 to 12. Preferably the pH of theaqueous solutions is adjusted to 4.5 to 11. The aqueous solutionsprepared as above are less irritating to the skin and have remarkablyexcellent surface activity even at low concentrations. More preferably,the pH of the aqueous solutions is adjusted to 5 to 8.

When the acyl group-containing composition of this invention is used inthe form of a solution, the content of the acyl group-containingcomposition is not particularly limited. The content can be 0.01 to 99%by weight and preferably 0.01 to 50% by weight, which is within therange that allows the composition to exert surface activity, dependingon the application for which it is used.

The aqueous solution containing the acyl group-containing compositionmay contain another surfactant, such as an anionic, nonionic, cationicor amphoteric surfactant, depending on the situation. Above all, thosecontaining a long chain N-acyl amino acid or a salt thereof as ananionic surfactant in the aqueous solution in such an amount that (A) anacyl group-containing composition and (B) a long chain N-acyl amino acidor the salt thereof are contained in the mass ratio (A)/(B) of 1/100 to100/1 in the aqueous solution are preferable.

The term “long chain N-acyl amino acid” herein used means an amino acidwith an acyl group derived from a saturated or unsaturated fatty acidwith 8 to 20 carbon atoms introduced to its amino group. The amino acidresidue in the long chain N-acyl amino acid may be an α-amino acid,β-amino acid, γ-amino acid or ω-amino acid and the amino group may be aN-methyl group or N-ethyl group. It does not matter which opticallyisomeric configuration the acidic amino acid has. It may be a D-isomer,L-isomer or racemate.

Examples of such amino acids include glutamic acid, asparagic acid,glycine, alanine, lanthionine, β-methyllanthionine, cyctathionine,diencholic acid, felinine, aminomalonic acid, β-oxyasparagic acid,α-amino-α-methylsuccinic acid, β-oxyglutamic acid, γ-oxyglutamic acid,γ-methylglutamic acid, γ-methyleneglutamic acid, γ-methyl-γ-oxyglutamicacid, α-aminoadipic acid, α,α′-diaminoadipic acid, β,β′-diaminoadipicacid, α-amino-γ-oxyadipic acid, α-aminopimelic acid,α-amino-γ-oxypimelic acid, β-aminopimelic acid, α-aminosuberic acid,α-aminosebacic acid and pantothenic acid.

The acyl group may be any acyl group as long as it is derived from asaturated or unsaturated fatty acid with 8 to 20 carbon atoms. It doesnot matter whether it is a straight-chain, branched-chain orcyclic-chain. From the viewpoint of biodegradability, it is preferablethat the a long chain N-acyl amino acid is a long chain N-acyl-L-aminoacid.

Typical examples of applications for which the acyl group-containingcomposition of this invention or aqueous solutions thereof are used are:raw materials for industrial cleaning agents and treatments, domesticdetergents (for clothes, kitchen, house, tableware, etc.), cosmetics,foods, medicines, emulsifying (polymerization) agents, agriculturalchemicals, textile processing agents (scouring agent, dye-assist agent,textile softener, water repellent), stainproofing agents, concreteadmixtures, printing inks, lubricating oils, antistatic agents,anti-fogging agents, lubricants, dispersants and deinking agents.

These are useful applications where the characteristics of thisinvention, such as less coloration in products, less irritation to theskin, surface activity at low concentrations, moisturizing performance,pigment dispersion stability, detergency, high emulsifying stability,low loading on environment due to biodegradability, are made good useof. When using the acyl group-containing composition of this inventionfor these applications, it is prepared into formulas (e.g. cosmeticcompositions) depending on the applications for which it is used. Theamount of the acyl group-containing composition blended in a formula isnot particularly limited, and it can be in the range of 0.01 to 99% byweight and preferably in the range of 0.01 to 50% by weight depending onthe application. The acyl group-containing composition of this inventioncan be used as solutions having a pH, for example ranging widely from 3to 12, preferably as solutions having a pH ranging from 4.5 to 11 andmore preferably as solutions having a pH ranging from 5 to 8 byadjusting the neutralization rate of the composition with a basicsubstance.

When using the acyl group-containing composition of this invention asformulas for various applications, it can take the form of a liquid, asolid, a gel, a paste or a mist depending on the purpose for which it isused.

The acyl group-containing composition of this invention and the aqueoussolution thereof are used as materials for cosmetics.

The term “cosmetics” herein used indicates the general term of quasidrugs and cosmetics stipulated in Pharmaceutical Affairs Law.Specifically, examples of quasi drugs include mouth refrigerants,underarm deodorants, talcum powders, hair growth stimulants, hairremovers, hair dye, permanent wave preparations, bath preparations,medicated cosmetics and medicated dentifrice. Examples of cosmeticsinclude: cleansing cosmetics such as toilet soaps, facial cleansingagents (in the cream/paste, liquid/gel, granule/powder, or aerosolform), shampoos and rinses; hair care cosmetics such as dyes, hairtreatments (in the form of cream, mist, oil, gel and others, includingsplit hair coating preparations), hair setting preparations (hair oils,hair setting lotions, curler lotions, pomade, stick pomade, bintsuke(hair setting) oil, hair spray, hair mist, hair liquid, hair foam, hairgel, water grease); basic cosmetics such as general skin cream, milkylotion (e.g. cleansing cream, cold cream, vanishing cream, hand cream),shaving creams (e.g. after shaving cream, shaving cream), skin lotions(e.g. hand lotions, general skin lotions), eau de colognes, shavinglotions (e.g. after shaving lotion, shaving lotion), cosmetic oils andface packs; makeup cosmetics such as face powders (cream powder, pressedpowder, powder, talcum powder, grease paint, baby powder, body powder,liquid powder), powder, foundation (cream, liquid, solid, etc.), cheekcolors, eyebrow color, eye cream, eye shadow and mascara; perfumes suchas general perfumes, grease perfumes and powder perfumes; fragrancepreparations of gel, liquid or ceramic containing potpourri type,deodorants and deodorizers; suntan/sunscreen cosmetics such assuntan/sunscreen creams, suntan/sunscreen lotions and suntan/sunscreenoils; manicure preparations such as nail cream, nail enamel and nailenamel remover; eye liners; lip cosmetics such as lip stick and lipcream; mouth preparations such as dentifrices; and bath preparationssuch as bath salts, bath oils and bubble baths. Among them, the formulasof the acyl group-containing composition of this invention are oftenused as materials for cleansing cosmetics, hair care cosmetics and basiccosmetics, and particularly suitably used as materials for cleansingcosmetics.

When using the acyl group-containing composition of this invention ascosmetic compositions, preferably the cosmetics include one or more theacyl group-containing compositions and a polyhydroxyl compound.

Examples of polyhydroxyl compounds, which have 2 or more hydroxyl groupsper molecule, include: divalent hydroxyl compounds such as ethyleneglycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol,1,3-butanediol, 1,4-butanediol, pentanediol, 1,6-hexanediol,cyclohexanediol, dimethylolcyclohexane, neopentyl glycol,1,8-octanediol, 2,2,4-trimethyl-1,3-pentanediol, isoprene glycol,3-methyl-1,5-pentanediol, sorbite, catechol, resorcin, hydroquinone,bisphenol A, bisphenol F, hydrogenated bisphenol A, hydrogenatedbisphenol F, dimerdiol, dimethylolpropionic acid, dimethylolbutanoicacid, tartaric acid, dihydroxytataric acid, mevalonic acid,3,4-dihydroxycinnamic acid, 3,4-dihydroxyhydrocinnamic acid,hydroxybenzoic acid, dihydroxystearic acid, dihydroxyphenylalanine andthe isomers thereof; trivalent polyhydroxyl compounds such as glycerol,trioxyisobutane, 1,2,3-butanetriol, 1,2,3-pentanetriol,2-methyl-1,2,3-propanetriol, 2-methyl-2,3,4-butanetriol,2-ethyl-1,2,3-butanetriol, 2,3,4-pentanetriol, 2,3,4-hexanetriol,4-propyl-3,4,5-heptanetriol, 2,4-dimethyl-2,3,4-petanetriol, 1,2,4-butanetriol, 1,2,4-pentanetriol, trimethylolethane, trimethylolpropane,diethanolamine, triethanolamine, trihydroxystearic acid; tetravalentpolyhydroxyl compounds such as pentaerythritol, erythritol,1,2,3,4-pentanetetrol, 2,3,4,5-hexanetetrol, 1,2,4,5-pentanetetrol,1,3,4,5-hexanetetrol, diglycerol and sorbitan; pentavalent polyhydroxylcompounds such as adonitol, arabitol, xylitol and triglycerol;hexavalent polyhydroxyl compounds such as dipentaerythritol, sorbitol,mannitol, iditol, inositol, dalsitol, talose and allose; the dehydrationcondensation products thereof; and polyglycerols.

Examples of such polyhydroxyl compounds also include saccharides: forexample, monosaccharides, such as tetrose such as erythrose, threose anderythrulose, pentose such as ribose, arabinose, xylose, lyxose, xyluloseand ribulose, hexose such as allose, altrose, glucose, mannose, gulose,idose, galactose, tarose, fructose, sorbose, psicose and tagatose; andoligosaccharides such as maltose, isomaltose, cellobiose, gentiobiose,meribiose, lactose, turanose, treharose, saccharose, mannitriose,cellotriose, gentianose, raffinose, melezitose, cellotetrose andstachyose.

Such polyhydroxyl compounds may be other saccharide residues such asheptose, deoxy-saccharides, amino-saccharides, thio-saccharides,seleno-saccharides, aldonic saccharides, uronic acid, sugar acid,ketaldonic acid, anhydrosugars, unsaturated sugars, sugar esters, sugarethers and glycoside, or polysaccharides such as starch, glycogen,cellulose, chitin and chitosan, or hydrolyzed products thereof. Thecombination of two kinds or more of these polyhydroxyl compounds mayalso be used. Preferable polyhydroxyl compounds are those with valenceof 3 or more.

Preferably, the cosmetics containing the acyl group-containingcomposition of this invention contain one kind or more acylgroup-containing compositions and a polyhydroxyl compound, wherein thecontent of the polyhydroxyl compound is 0.001 to 40% by weight and thecontent of the acyl group-containing composition is 10/1 to 1/100 interms of the weight ratio to the polyhydroxyl compound. If the contentof the polyhydroxyl compound is less than 0.001% by weight, thecosmetics leave the skin feeling less moist and the moisturizing effectof the composition is hard to exert, whereas if the content of thepolyhydroxyl compound is higher than 40% by weight, the cosmetics leavethe skin feeling stickier. If the amount of the acyl group-containingcomposition is less than 1/100 in terms of the weight ratio to thepolyhydroxyl compound, the cosmetics are likely to give users feeling ofstickiness coming from the polyhydroxyl compound and other ingredients,whereas if the amount is more than 10/1, the cosmetics are likely togive users feeling of stickiness coming from the acyl group-containingcomposition. More preferably, the content of the polyhydroxyl compoundis 0.1 to 30% by weight and the content of the acyl group-containingcomposition is 5/1 to 1/50 in terms of the weight ratio to thepolyhydroxyl compound. Much more preferably, the content of the acylgroup-containing composition is 5/1 to 1/20 in terms of the weight ratioto the polyhydroxyl compound.

In the cosmetics containing the acyl group-containing composition ofthis invention, use of oil ingredients is preferable, because theyprovide moisturizing and emollient effects on the skin. As oilingredients, either liquid oil or solid fat may be used and thosecommonly used as ingredients for cosmetics or medicines for externalapplication may also be used.

Examples of oil ingredients include volatile and non-volatile ones,specifically they include: oils and fats such as avocado oil, almondoil, olive oil, cacao oil, sesame oil, safflower oil, soybean oil,camellia oil, persic oil, castor oil, grape seed oil, macadamia nut oil,mink oil, cottonseed oil, Japan tallow, coconut oil, yolk oil, palm oil,palm stone oil, glyceryl triisooctanoate, glyceryl tri-2-ethylhexanoateand cholesterol fatty acid ester; waxes such as spermaceti, carnaubawax, candellia wax, jojoba seed oil, bee wax, lanolin and thederivatives thereof; hydrocarbons such as liquid paraffin, paraffin,vaseline, ceresin, microcrystalline wax, squarane and squalene; higherfatty acids such as lauric acid, myristic acid, palmitic acid, stearicacid, isostearic acid, oleic acid, behenic acid, undecylenic acid,lanolin fatty acid, hard lanolin fatty acid and soft lanolin fatty acid;higher alcohols such as lauryl alcohol, cetyl alcohol, cetostearylalcohol, stearyl alcohol, isostearyl alcohol, 2-octyldodecanol, oleylalcohol, behenyl alcohol, lanolin alcohol, hydrogenated lanolin alcoholand hexyldecanol; higher alcohol fatty acid esters such as isopropylmyristate, octadecyl myristate, 2-octyldodecyl myristate, cetyl2-ethylhexanoate, diisostearyl malate, isostearyl isostearate,isostearyl cholesteryl ester and butylstearate; and silicone oils suchas (di)methyl silicone, methyl phenyl silicone, amino modified siliconeand cyclic silicone. These oil ingredients may be used in combination oftwo kinds or more.

Cosmetics that contain the acyl group-containing composition of thisinvention can be produced by mixing, while stirring, an acylgroup-containing composition, a polyhydroxyl compound and, if necessary,water and an oil ingredient. Particularly when producing an oilingredient-containing emulsion such as a milky lotion, a later-describedprocess is preferably used in which cosmetics are produced byemulsifying an acyl group-containing composition, a polyhydroxylcompound and an oil- and gelatinous-composition that contains an oilingredient.

Specifically, oil- and gelatinous-compositions are very easily broughtto the stable emulsified and dispersed state when they are stirred withwater added thereinto; and therefore, cosmetics are produced only byadding water to oil- and gelatinous-compositions. To produce cosmeticsthat further excel in a moist feeling or moisture retaining effect andare in the stable emulsified state, a process is preferable in which notonly water, but also a polyhydroxyl compound, a higher alcohol or oilingredients are properly added to the above described gelatinouscomposition depending on the situation.

The cosmetics that contain the acyl group-containing composition of thisinvention obtained as above are characterized by excellent moistfeeling, excellent moisture retaining effects and being capable ofkeeping a very stable emulsified state over time.

Cosmetics that contain the acyl group-containing composition of thisinvention can be applied to, for example, a milky lotion, a cream, alotion and a skin lotion, along with those intended to cleanse the skin,such as a cleansing lotion, a facial cleansing preparations and a bodyshampoo. Cosmetics that contain the acyl group-containing composition ofthis invention can take various forms such as a liquid, a paste, a geland an aerosol, depending on desire.

When using the acyl group-containing composition of this invention as ablended composition, preferably the composition is used as a gelatinouscomposition that contains the acyl group-containing composition, apolyhydroxyl compound and oil ingredients.

Examples of polyhydroxyl compounds having 2 or more hydroxyl groups permolecule and applicable to the gelatinous composition of this inventioninclude those described above. In the gelatinous composition of thisinvention, polyhydroxyl compounds with valency of 3 or more arepreferably used.

Polyhydroxyl compounds may be used in combination of two kinds or moreand polyhydroxyl compounds with different valencies, for example,polyhydroxyl compounds of 2-valency and 3-valency may also be used incombination.

Examples of oil ingredients used in the gelatinous composition of thisinvention include those described above.

The gelatinous composition of this invention contains one kind or moreacyl group-containing compositions, one or more polyhydroxyl compoundshaving 2 or more hydroxyl groups per molecule and one or more oilingredients, and preferably the water content in the gelatinouscomposition is 50% by weight or less and the composition of thegelatinous composition is such that 1) the total amount of acylgroup-containing composition(s) is 0.1 to 40% by weight, 2) the totalamount of polyhydroxyl compound(s) is 1 to 60% by weight and 3) thetotal amount of oil ingredient(s) is 1 to 95% by weight. The contents ofacyl group-containing compositions, polyhydroxyl compounds and oilingredients herein mentioned each indicate the total sum of therespective ingredients. If the water content is outside this range, thegel state of the composition cannot sometimes be kept stable. The watercontent is more preferably 30% by weight or less and much morepreferably 20% by weight or less.

Even if the content of each ingredient is outside the above describedrange, the composition can sometimes take the gel form. However, suchgelatinous composition can sometimes be poor in stability due to theseparation of oil ingredients, be poor in gel forming performance, havedecreased detergency, or have an unfavorable after feel depending on thepurpose for which it is used.

In the gelatinous composition of this invention that contains an acylgroup-containing composition(s), the composition of acylgroup-containing composition(s), polyhydroxyl compound(s) and oilingredient(s) is more preferably such that 1) the total amount ofsurfactant(s) is 1 to 25% by weight, 2) the total amount of polyhydroxylcompound(s) is 5 to 40% by weight and 3) the total amount of oilingredient(s) is 20 to 80% by weight and much more preferably 1) thetotal amount of surfactant(s) is 3 to 15% by weight, 2) the total amountof polyhydroxyl compound(s) is 5 to 30% by weight and 3) the totalamount of oil ingredient(s) is 30 to 70% by weight.

In the production of the gelatinous composition of this invention, toobtain one whose appearance is transparent, it is preferable to allowthe difference in refractive index at 20° C. between the water phase,which is composed of an acyl group-containing composition(s), apolyhydroxyl compound(s) and water, and the oil phase, which is composedof an oil ingredient(s), to be ±0.05 or less. If the difference inrefractive index between the two phases is outside the range, one whoseappearance is transparent cannot be obtained. The closer the differencein refractive index between the two phases comes to 0, the better. Morepreferably the difference is ±0.03 or less and much more preferably 0.01or less. It is particularly preferable that the difference is 0.

The gelatinous composition of this invention is produced by mixing,while stirring, an acyl group-containing composition(s), a polyhydroxylcompound(s), an oil ingredient(s) and, depending on the situation, waterunder high shear stress. A preferred production process is to fully mix,while stirring, the ingredients other than the oil ingredient(s) andthen add the oil ingredient(s) to the mixture little by little.

The gelatinous composition of this invention obtained as above hasexcellent characteristics of: 1) being highly capable of forming agelatinous composition and keeping a stable gel state over time, 2)having a wide range of viscosity, 3) being easily fine-dispersed andbrought to an emulsion state when water is added, and 4) being easilywashed with water when used as a cleansing agent such as a cleansingpreparation and leaving no residue on the skin while leaving the skinfeeling refreshed.

Typical examples of suitable applications of the gelatinous compositionof this invention are: various external preparations, gel basematerials, and cleaners. Examples of external preparations include:various kinds of cosmetics such as a cream or a gel for facialwashing/cleansing, a cold cream, a vanishing cream or a moisturizingcream; skin or hair care cosmetics such as massage gel and hairdressings; and drugs such as antiphlogistics or gelatinouspharmaceuticals, or vermin repellent. Examples of inclusion/carrier typeof gel base materials include: sustained-release perfume gels in whichperfume or an absorbent/adsorbent such as activated carbon isincluded/dispersed; deodorizing gel base materials; and in addition,pesticides and bath agents in which the water-dispersibility of thematerials is made good use of. The gelatinous composition of thisinvention can also be used as cleaners, in which its characteristic ofabsorbing oil ingredients is made good use of, such as cleaners for oilstains in the kitchen and around gas ranges, cleaners for oil stains onmachines, cleaners for hands, and cleaners for coated surfaces on metalsof cars etc., coated surfaces on woods of family Buddhistaltars/Buddhist altar fittings/wardrobes/desks, etc., plastic surfacesof electric appliances such as TVs/personal computers and glasssurfaces.

When used for cleansing agents the gelatinous composition that containsthe acyl group-containing composition of this invention, those whoseviscosity at 25° C. is in the range of 1000 to 200000 mPa·s arepreferably used because they spread smoothly when applied to the skinetc. The gelatinous compositions whose viscosity at 25° C. is in therange of 3000 to 60000 mPa-s are more preferably used

When using the acyl group-containing composition of this invention as ablended composition, preferably it is used as a dispersant compositionthat contains the acyl group-containing composition.

The dispersant composition that contains the acyl group-containingcomposition of this invention prevents hydrophilic and/or hydrophobicpowder from aggregating, and therefore, excels in dispersion stability.Such a dispersant composition can be used with various pigments in thefollowing application fields, specifically including, pigments in thewater-based/non-water-based coating fields; those in thepigment/printing ink fields, such as titanium white, red iron oxide,aluminum powder, talc, carbon black, azo pigment and phthalocyanine,those in the pigment/cosmetic fields (including bath agents), such ascarbon black, azo pigment and phthalocyanine; those in thepigment/reinforced rubber, plastic fields, such as talc, (fine-grained)titanium oxide, titanium, mica, alumina, bentonite, red iron oxide, zinclaurate, zinc stearate, zinc oxide, chromium oxide, ultramarine,Prussian blue, iron oxide, kaolin, sericite, safflower pigment andcochineal extract; those in pigment/fiber, dyeing fields, such as clay,calcium carbonate, silica, carbon black and phthalocyanine; pigmentprinting, disperse dye/cement, concrete fields; cement/coated papercoating color fields; pigment/optical catalyst fields, such as calciumcarbonate, talc, titanium oxide and clay; and ultra fine particletitanium oxide. Examples of other pigments include: inorganic pigmentssuch as cobalt blue, chromium green, chromium oxide, silicic acidanhydride and magnesium aluminate silicate; organic pigments such aspowdered skin of fruits or nuts, powdered Japanese cypress, polyethylenepowder, polymethylsilsesquioxane powder, Hansa yellow, benzidine yellow,permanent yellow, tartrazine lake, quinone yellow, Sudan 1 and permanentorange; metal powder pigments such as bronze powder; inorganicfluorescent pigments such as zinc sulfide, zinc silicate, zinc cadmiumsulfide, calcium sulfide, strontium sulfide and calcium tungstate; andother known organic fluorescent pigments.

The dispersant composition that contains the acyl group-containingcomposition of this invention may or may not contain water. It may takethe form of a solid, a liquid or a paste which is simply a mixture ofthe acyl group-containing composition, a pigment, etc. It can be used inthe form of: pigment coated with the acyl group-containing composition;pigment to which the acyl group-containing composition is sealed using apolymer etc. as a matrix; pigment bearing the acyl group-containingcomposition; or pigment chemically binding to the acyl group-containingcomposition directly or via a crosslinking agent or the like.

In the dispersant composition that contains the acyl group-containingcomposition of this invention, preferably the percentage of the acylgroup-containing composition to a pigment is 0.01% by weight or greater,more preferably 0.1% by weight or greater, and much more preferably 1%by weight or greater. A larger percentage of the acyl group-containingcomposition to the pigment in the dispersant composition makes thedispersant composition more stable, as long as there is no otherproblem. However, if the amount exceeds 500% by weight, there cansometimes be created problems depending on the application; for example,when the dispersant composition is applied to ink, the water resistanceof the ink can sometimes deteriorate.

A pigment dispersant can be produced with the dispersant composition ofthis invention by mixing, while stirring, the dispersant composition, apigment and a dispersion medium with a dispersion mixer commonly usedsuch as a ball mill, roll mill, sand mill, flow mill, dyno-mill,attritor, homomixer, homogenizer or high-speed disperser. The mixingwhile stirring can be carried out at an ordinary temperature or withheating, depending on the situation.

The acyl group-containing composition of this invention is also usefulfor cleansing agent compositions. With the acyl group-containingcomposition of this invention, a cleansing composition can be providewhich is capable of decreasing surface tension even at lowconcentrations, is less irritating to the skin, and excels in formingproperties and a refreshing afterfeel. The acyl group-containingcomposition of this invention is characterized in that when it isdissolved in water to prepare a dilute aqueous solution and used to wipesebum off one's face, it leaves the face skin feeling smooth. Further,because the composition itself has a moisture retention performance, itcan be used a moisturizer.

The acyl group-containing composition of this invention can be usedtogether with various kinds of base materials depending on theapplication and purpose for which it is used.

Specifically, the acyl group-containing composition of this inventioncan be used together with:

-   -   a dispersant such as netural gum, such as gum arabic or traganth        gum, glucoside, such as saponin, cellulose derivatives such as        methyl cellulose, carboxy cellulose or hydroxymethyl cellulose,        natural polymer, such as lignin sulfonate or shellac, anionic        polymer, such as polyacrylate, salt of styrene-acrylic acid        copolymer, salt of vinylnaphthalene-maleic acid copolymer,        sodium salt or phosphate of β-naphthalenesulfonic acid formalin        condensation product or nonionic polymer, such as        polyvinylalcohol, polyvinylpirrolidone or polyethylene glycol;    -   an anionic surfactant such as a fatty acid salt (soap),        alkylsulfonic acid ester salt (AS), polyoxyethylenealkyl ether        sulfate ester salt (AES), α-olefin sulfonat (AOS), alkylbenzene        sulfonate, alkylnaphthalene sulfonate, alkyl sulfonate (SAS),        dialkyl sulfosuccinate, α-sulfonated fatty acid salt, long chain        N-acyl amino acid salt, N-acyl-N-methyl taurinate, sulfated fat        and oil, polyoxyethylene styrenated phenylether sulfate, alkyl        phosphate, polyoxyethylene alkyl ether phosphate,        polyoxyethylene alkyl phenyl ether phosphate or naphthalene        sulfonate formalin condensation product;    -   an amphoteric surfactant such as an alkyl betaine, alkyl amide        betaine, alkyl sulfo betaine or imidazolinium betaine;    -   a nonionic surfactant such as fatty acid alkylol amide, alkyl        amine oxide, polyoxyethylene alkyl ether (AE), polyoxyethylene        alkyl phenyl ether, polyoxyethylene polystyryl phenyl ether,        polyoxyethylene polyoxypropylene glycol, polyoxyethylene        polyoxypropylene alkyl ether, polyhydric alcohol fatty acid        partial ester, polyoxyethylene polyhydric alcohol fatty acid        partial ester, polyoxyethylene fatty acid ester, polyglycerol        fatty acid ester, polyoxyethylene hardened castor oil,        polyoxyethylene alkyl amine or triethanol amine fatty acid        partial ester;    -   a cationic surfactant such as primary to tertiary fat amine        salt, alkyl ammonium chloride salt, tetraalkyl ammonium salt,        trialkyl benzyl ammonium salt, alkyl pyridinium salt, alkyl        hydroxyethyl imidazolinium salt or dialkyl morpholinium salt;    -   a polymer surfactant such as sodium alginate, starch derivative        or gum tragacanth;    -   a natural surfactant lecithin, lanolin, cholesterol or saponin;    -   a fatty and oil such as avocado oil, almond oil, olive oil,        cacao oil, sesame oil, safflower oil, soybean oil, camellia oil,        persic oil, castor oil, mink oil, cottonseed oil, Japan tallow,        coconut oil, yolk oil, palm oil, palm stone oil, synthesized        triglyceride or jojoba oil;    -   a hydrocarbon such as liquid paraffin, vaseline, ceresin,        microcrystalline wax or isoparaffin;    -   a wax such as bees wax, spermaceti wax, lanolin, carnauba wax,        candellia wax or a derivative thereof;    -   a higher fatty acid such as lauric acid, myristic acid, palmitic        acid, stearic acid, isostearic acid, oleic acid, behenic acid,        undecylenic acid, lanolin fatty acid, hard lanolin fatty acid or        soft lanolin fatty acid;    -   a higher alcohol such as lauryl alcohol, cetanol, cetostearyl        alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol,        lanolin alcohol, hydrogenated lanolin alcohol and hexyldecanol        or octyldecanol;    -   an ester oil such as isopropyl myristate, butyl stearate or        others;    -   a volatile or nonvolatile oil such as metallic soap, or silicone        oils such as straight silicone oil or modified silicone oil;    -   a polyol such as glycerol, diglycerol, polyglycerol,        1,3-butanediol, propanediol or polyethylene glycol;    -   a moisture retaining agent such as trimethylglycine, sorbitol,        raffinose, pyrrolidone carboxylate, lactate, hyaluronate or        ceramide;    -   a water- or oil-soluble polymer such as hydroxyethyl cellulose,        carboxymethyl cellulose, hydroxyethyl cellulose hydroxypropyl        trimethyl ammonium chloride ether, methyl cellulose, ethyl        cellulose, hydroxypropyl cellulose, methyl hydroxypropyl        cellulose, soluble starch, carboxymethyl starch, methyl starch,        alginic acid propylene glycol ester, polyvinyl alcohol,        polyvinyl pyrrolidone, polyvinyl methyl ether, carboxyvinyl        polymer, polyacrylate, gum guar, locust bean gum, quince seed,        carrageenan, galactan, gum arabic, pectin, mannan, starch,        xanthane gum, dextran, suucinoglucan, curdlan, hyaluronic acid,        gelatin, casein, albumin, collagen, methoxyethylene maleic        anhydride copolymer, amphoteric methacrylate ester copolymer,        poly dimethyl methylenepiperidium chloride, polyacrylate ester        copolymer, polyvinyl acetate, nitrocellulose or silicone resin;    -   a thickening or lathering ingredient such as polyethylene glycol        fatty acid ester, polyoxyethylene fatty acid ester methyl        glycoside or tetradecene sulfonate;    -   a sequestering agent such as ethylenediamine tetraacetate or a        salt thereof, hydroxyethylenediamine triacetate or a salt        thereof, phosphoric acid, ascorbic acid, succinic acid, gluconic        acid, polyphosphate, metaphosphate or hinokitiol;    -   a preservative such as paraoxybenzoate ester, benzoic acid or a        salt thereof, phenoxyethanol or hinokithiel;    -   a pH adjustor such as citric acid, malic acid, adipic acid,        glutamic acid or aspartic acid; and    -   others such as an anti-dandruff/itching relief agent such as        trichlorocarbanilide, salicylic acid, zinc pyrithione or        iropropylmethylphenol    -   an ultraviolet ray absorber such as benzophenone derivatives,        paraminobenzoic acid derivatives, paramethoxycinnamic acid        derivatives, salicylic acid derivatives or others;    -   a whitening agent such as albutin, kojic acid, ascorbic acid,        hinokithiol and derivatives thereof;    -   a blood circulation improver such as swertia herb extract,        cepharathine, vitamine E or a derivative thereof, or γ-oryzanol;    -   a local excitatory agent such as capsicum tincture, ginger        tincture, cantharides tincture or benzyl nicotinate;    -   a nutrient such as various types of vitamins or amino acids;    -   a female hormone;    -   a hair root activating agent;    -   an antiinflammative such as glycyrrhizinic acid, glycyrrhizinic        acid derivative, allantoin, azulene, aminocaproic acid or        hydrocortisone;    -   an astringent such as zinc oxide, zinc sulfate, allantoin        hydroxyaluminum, aluminum chloride, zinc sulfocarbolate or        tannic acid;    -   a tonic such as menthol or camphor;    -   antihistamine;    -   an antioxidant such as silicone substance such as polymer        silicone or cyclic silicone, tocopherols, BHA, BHT, gallic acid        and NDGA; and    -   purified water.

Particularly, the combination with fatty acid diethanol amide,polyoxyethylene methyl dioleate glucoside, distearate polyethyleneglycol, tetradecene sulfonate, miristates or miristyldimethyl amine isuseful in that it increases the viscosity and forming properties of thecomposition, and besides the combination with an amphoteric surfactantis very useful in that it further decreases irritation of the skin.

In the following this invention will be described in more detail givingexamples and the like, which are not intended to limit this invention.

The evaluations used in the examples of this invention are as follows.

(A) Determination of acyl compound, dehydrated acyl compound, free fattyacid, and long chain N-acyl acidic amino acid or the salt thereof.

Ingredients were separated by high performance liquid chromatography(HPCL) over an ODS column (YMC-Pack, AM-312) using, as an eluent, amethanol/water/phosphoric acid system (methanol/1,4-dioxane/water/85%phosphoric acid=2450/60/490/1 (volume ratio)) and determination of theingredients was carried out with an ultraviolet detector (SHIMADZUCORPORATION; SPD-10A) at 205 nm and a differential refractive indexdetector (SHIMADZU CORPORATION; RID-10A). Ingredients other thandehydrated acyl compounds were detected with the differential refractiveindex detector and dehydrated acyl compounds with the ultravioletdetector (because the amount of dehydrated acyl compounds existing wasso small that it was hard to detect with a differential refractive indexdetector).

In the examples, the content of free fatty acid and that of long chainN-acyl acidic amino acid or the salt thereof were indicated in terms of% by weight to acyl compounds. Dehydrated acyl compounds were confirmedwith an ultraviolet detector at 205 nm and their content was indicatedby % by peak area to acyl group-containing compounds.

The term “purity of acyl group-containing composition” shown below meansthe percentage of the weight of acyl compound, as a product, to thetotal weight of acyl group-containing composition.

Evaluation criteria are as follows.

(Evaluation Criteria for Purity of Acyl Group-Containing Composition)

-   -   Purity is 85% or more ⊚    -   Purity is 70% to less than 85% ◯    -   Purity is less than 70% x        (Evaluation Criteria for Free Fatty Acid Content)    -   Content is 3% or more x    -   Content is 1% to less than 3% ◯    -   Content is less than 1% ⊚        (Evaluation Criteria for Dehydrated Acyl Compound Content)    -   Content is 5% or more x    -   Content is 1% to less than 5% ◯    -   Content is less than 1% ⊚        (Evaluation Criteria for Content of Long Chain N-acyl Acidic        Amino Acid or the Salt Thereof)    -   Content is 15% or more x    -   Content is 1% to less than 10% ◯    -   Content is less than 1% ⊚        (B) Measurement of Transmittance of the Aqueous Solution

The transmittances at 430 nm and 550 nm were measured with a cell ofoptical path length 10 mm of a 20% by weight (pH 10) aqueous solutionprepared by neutralizing an acyl group-containing composition withsodium hydroxide.

The evaluation criteria were as follows.

-   -   Transmittances both at 430 nm and at 550 nm are 95% or more ⊚    -   Transmittances both at 430 nm and at 550 nm are 90% to less than        95% ◯    -   Transmittances either of or both at 430 nm and at 550 nm are        less than 90% Δ        (C) Stability of the Gelatinous Composition

Gelatinous compositions were kept at 40° C. and their state was observedafter one month. The stability was evaluated for each composition inaccordance with the following criteria.

-   -   ◯: The state is not changed and good    -   Δ: Separation is observed a little    -   x: Separation is apparent        (D) Afterfeel of Gelatinous Composition

Each gelatinous composition was applied to 5 panelists' hands and rubbedwell into the skin to conduct a sensory test. And the afterfeel of eachcomposition after washing the hands with water was evaluated inaccordance with the following criteria.

-   -   ◯: The number of the panelists who feel that the composition        does not leave the skin feeling sticky and has a good afterfeel        is 3 or more    -   Δ: The number of the panelists who feel that the composition        does not leave the skin feeling sticky and has a good afterfeel        is 1 or 2    -   x: The number of the panelists who feel that the composition        does not leave the skin feeling sticky and has a good afterfeel        is 0        (E) Measurement of Viscosity

The viscosity of each gelatinous composition was measured at 25° C. witha B type viscometer (Brookfield; LVDVE115) and evaluated according tothe following five ranks.

The viscosity of the gelatinous composition is 200,000 mPa or more

The viscosity of the gelatinous composition is 60,000 mPa or more andless than 200,000 mPa

The viscosity of the gelatinous composition is 3,000 mPa or more andless than 60,000 mPa

The viscosity of the gelatinous composition is 1,000 mPa or more andless than 3,000 mPa

The viscosity of the gelatinous composition is less than 1,000 mPa

(F) Ease of Spreading at the Time of Application

Each cleansing agent was applied to 5 panelists to conduct a sensorytest. And the ease of its spreading was evaluated according to thefollowing criteria.

-   -   ◯: The number of the panelists who feel that the ease of        spreading of the cleansing agent is good at the time of        application is 3 or more    -   Δ: The number of the panelists who feel that the ease of        spreading of the cleansing agent is good at the time of        application is 1 or 2    -   x: The number of the panelists who feel that the ease of        spreading of the cleansing agent is good at the time of        application is 0        (G) Appearance

Each gelatinous composition was evaluated visually (based on“transparent”, “translucent” or “separated”).

(H) Measurement of Refractive Index

The refractive index of each phase at 20° C. was measured by arefractometer. The difference in refractive index between the oil phaseand the water phase was evaluated according to the following 4 rankcriteria.

The difference in refractive index between the oil phase and the waterphase is 0.05 or more

The difference in refractive index between the oil phase and the waterphase is 0.03 or more and less than 0.05

The difference in refractive index between the oil phase and the waterphase is 0.01 or more and less than 0.03

The difference in refractive index between the oil phase and the waterphase is less than 0.01

(I) Stability of Cosmetics

Cosmetics were kept at 40° C. and their state was observed after onemonth. The stability was evaluated for each cosmetic in accordance withthe following criteria.

-   -   ◯: The state is not changed and good    -   Δ: Separation is observed a little    -   x: Separation is apparent        (J) Afterfeel of Cosmetics

Each cosmetic was applied to 5 panelists' hands to conduct a sensorytest. And the afterfeel of each cosmetic (sticky feeling, moist feeling)was evaluated in accordance with the following criteria.

-   -   ◯: The number of the panelists who feel that the cosmetic does        not leave the skin feeling sticky, do leave the skin feeling        moist and has a good afterfeel is 3 or more    -   Δ: The number of the panelists who feel that the cosmetic does        not leave the skin feeling sticky, do leave the skin feeling        moist and has a good afterfeel is 1 or 2    -   x: The number of the panelists who feel that the cosmetic does        not leave the skin feeling sticky, do leave the skin feeling        moist and has a good afterfeel is 0

In the following this invention will be described in detail givingexamples.

EXAMPLE 1

(Reaction Step)

First, 9.1 g (0.05 mol) of L-lysine hydrochloride was mixed in 57 g ofwater. Then, 31.1 g (0.1 mol) of N-lauroyl-L-glutamic acid anhydride wasadded to the mixed solution under stirring over 2 hours, while adjustingthe pH of the mixed solution in the range of 10 to 11 using a solutionof 25% sodium hydroxide in water and keeping the reaction temperature at5° C., to allow the reaction to progress.

(Acid-Precipitation and Layer-Separation Step)

After continuing another 30-minute stirring, tertiary butanol was addedso that its concentration in the mixed solution was 20% by weight, and75% sulfuric acid was added dropwise to adjust the pH of the solution to2 while adjusting the temperature of the solution to 65° C. Aftercompletion of the sulfuric acid addition, stirring was stopped, and themixed solution was left stand at 65° C. for 20 minutes so that thesolution was separated into an organic layer and a water layer. Then theorganic layer was isolated.

(Washing Step)

Tertiary butanol and water were added to the isolated organic layer toprepare a mixed solution having a composition of acyl compound/tertiarybutanol/water=33/25/42 (% by weight). The mixed solution was stirred at65° C. for 20 minutes. After stopping stirring, the mixed solution wasleft stand at 65° C. for 20 minutes so that the solution was separatedinto an organic layer and a water layer. Then the operation of washingthe resultant organic layer with water was repeated to remove thesolvent from the organic layer. Thus, 34.6 g of acyl group-containingcomposition was yielded. The analytical results are shown in Table 1.

EXAMPLE 2

The same steps as those of Example 1 were carried out under the sameconditions except that in the reaction step, a mixed solution of waterand tertiary butanol (concentration of tertiary butanol was 20% byweight) was used instead of water and N-lauroyl-D-glutamic acidanhydride was used instead of N-lauroyl-L-glutamic acid anhydride toyield 33.8 g of acyl group-containing composition. The analyticalresults are shown in Table 1.

EXAMPLE 3

The same steps as those of Example 1 were carried out under the sameconditions except that in the reaction step, 7.2 g of octanediamine wasused instead of 9.1 g of L-lysine hydrochloride, the reactiontemperature was changed to 55° C. and the pH range to 11 to 12 to yield32.9 g of acyl group-containing composition. The analytical results areshown in Table 1.

EXAMPLE 4

The same steps as those of Example 1 were carried out under the sameconditions except that in the reaction step, 33.9 g ofN-myristoyl-L-glutamic acid anhydride was used instead of 31.1 g ofN-lauroyl-L-glutamic acid anhydride, the reaction temperature waschanged to 15° C. and the pH range to 12 to 13 to yield 37.1 g of acylgroup-containing composition. The analytical results are shown in Table1.

EXAMPLE 5

The same steps as those of Example 1 were carried out under the sameconditions except that in the reaction step, 31.1 g ofN-cocoyl-L-glutamic acid anhydride was used instead of 31.1 g ofN-lauroyl-L-glutamic acid anhydride and 3.0 g of ethylenediamine wasused instead of 9.1 g of L-lysine hydrochloride to yield 29.0 g of acylgroup-containing composition. The analytical results are shown in Table1.

EXAMPLE 6

The same steps as those of Example 1 were carried out under the sameconditions except that in the reaction step, 3.53 g ofN-palmitoyl-L-asparagic acid anhydride was used instead of 31.1 g ofN-lauroyl-L-glutamic acid anhydride and a mixed solution of water andtoluene (concentration of toluene was 30% by weight) was used instead ofwater and 30° C. of the reaction temperature was used instead of 5° C.to yield 38.3 g of acyl group-containing composition. The analyticalresults are shown in Table 1.

COMPARATIVE EXAMPLE 1

Just like Example 9 described in JP-A-2002-167313, 31.1 g (0.1 mol) ofN-lauroyl-L-glutamic acid anhydride was added to 400 mL of toluene andstirred at 95° C. Then, 3.7 g (0.05 mol) of 1,3-propanediamine was addeddropwise to the mixed solution over 2 hours. After completing theaddition of 1,3-propanediamine, the mixed solution was stirred 1 hour,and toluene was distilled off from the solution to obtain 33.1 g of anacyl group-containing composition. It was then purified bychromatography to yield 23.0 g of acyl group-containing composition. Theanalytical results are shown in Table 1.

COMPARATIVE EXAMPLE 2

The same operations as those of comparative Example 1 were carried outunder the same conditions except that 7.3 g of L-lysine was used insteadof 3.7 g of 1,3-propanediamine to yield 25.0 g of acyl group-containingcomposition. The analytical results are shown in Table 1. TABLE 1 FreeN-acyl acidic N-acyl acidic fatty Transmittance amino amino acidReaction Reaction pH Product Dehydrate acid of 20% aqueous acid Exampleanhydride Reactant solvent temp. at reaction purity content contentsolution content Example 1 N-lauroyl-L- L-lysine Water  5° C. 10-11 ⊚ ⊚⊚ ⊚ 1˜10% glutamic acid hydrochloride anhydride Example 2 N-lauroyl-D-L-lysine Water/  5° C. 10-11 ⊚ ⊚ ⊚ ⊚ 1˜10% glutamic acid hydrochloridetertiary anhydride butanol Example 3 N-lauroyl-L- Octanediamine Water55° C. 11-12 ⊚ ⊚ ⊚ ⊚ 1˜10% glutamic acid anhydride Example 4N-myristoyl- L-lysine Water 15° C. 12-13 ⊚ ⊚ ⊚ ⊚ 1˜10% L-glutamichydrochloride acid anhydride Example 5 N-cocoyl-L- Ethylenediamine Water 5° C. 10-11 ⊚ ⊚ ⊚ ⊚ 1˜10% glutamic acid anhydride Example 6N-palmitoyl- L-lysine Water/ 30° C. 10-11 ⊚ ⊚ ⊚ ⊚ 1˜10% L-asparagichydrochloride Toluene acid anhydride Comparative N-lauroyl-L- 1,3-Toluene 90° C. — ◯ X ⊚ X <0.5% Example 1 glutamic acid propanediamineanhydride Comparative N-lauroyl-L- L-lysine Toluene 90° C. — ◯ X ⊚ X<0.5% Example 2 glutamic acid anhydride

EXAMPLE 7

The composition obtained in Example 1 was neutralized with sodiumhydroxide to prepare an aqueous solution of solid content 30% by weightand pH 6.5. The aqueous solution was dried to produce powder ofneutralized acyl group-containing composition.

EXAMPLE 8

The composition obtained in Example 5 was neutralized with sodiumhydroxide to prepare an aqueous solution of solid content 30% by weightand pH 7.5. The aqueous solution was dried to produce powder ofneutralized acyl group-containing composition.

EXAMPLES 9 TO 22, COMPARATIVE EXAMPLES 3 TO 6

Gelatinous compositions shown in Table 2 were produced, and thestability, utility, viscosity and transparency were evaluated for eachof the compositions. The results are shown in Table 2. The compositionare shown in % by weight.

(Production Process)

All of the gelatinous compositions were prepared by the followingprocess.

The ingredients other than oil ingredients were mixed at 70° C. whilestirring the mixture. Then, the oil ingredients were slowly addeddropwise to the mixture while stirring. The mixture was further stirredand cooled to yield a gelatinous composition. TABLE 2 Ingredient (wt %)Example 9 Example 10 Example 11 Example 12 Example 13 Example 14 Example15 Acyl-group-containing 4 7.1 6.8 1 1 composition of Example 7Acyl-group-containing 5 2 composition of Example 8 Sodium 2lauraylglutamate Sodium lauryl diphenyl ether disulfonatePolyoxyethylene (5) 3 lauryl ether Glycerol 30 28 21 24 31.2 18 20Diglycerol Sorbitol POE (20) methyl glycoside Sucrose Purified water 415.9 4 9.2 7.8 10 13 Liquid paraffin Isopropyl myristate 70 Isostearyl65 isostearate Grape seed oil TEG + Silicone (10CS) Squarane Olive oil60 49 Silicone (10CS) Glyceryltri-2- 60 60 34 ethylhexanoicacidLow-boiling point 34 silicone Stability ◯ ◯ ◯ ◯ ◯ ◯ ◯ Appearancetransparent translucent transparent transparent transparent transparenttranslucent Afterfeel ◯ ◯ ◯ ◯ ◯ ◯ ◯ Difference in <0.01 0.05 0.03 <0.01<0.01 <0.01 0.05 refractive index Viscosity (Pa · s) >200 3-60 60-2003-60 3-60 3-60 3-60 Spreading X ◯ Δ ◯ ◯ ◯ ◯ Ingredient (wt %) Example 16Example 17 Example 18 Example 19 Example 20 Example 21 Example 22Acyl-group-containing 6 1 5 1 5 6 composition of Example 7Acyl-group-containing 3 composition of Example 8 Sodium 3lauraylglutamate Sodium lauryl diphenyl ether disulfonatePolyoxyethylene (5) 2 lauryl ether Glycerol 32 14.3 20 20 12 Diglycerol19 Sorbitol 30 POE (20) methyl 4.8 glycoside Sucrose Purified water 4 24.6 4 2 0 22 Liquid paraffin 77 Isopropyl myristate Isostearylisostearate Grape seed oil 60 TEG + Silicone (10CS) Squarane 70 60 Oliveoil 60 Silicone (10CS) 60 Glyceryltri-2- 75.3 ethylhexanoicacidLow-boiling point silicone Stability ◯ ◯ ◯ ◯ ◯ ◯ ◯ Appearance opaquetransparent transparent transparent transparent opaque transparentAfterfeel ◯ ◯ ◯ ◯ ◯ ◯ ◯ Difference in 0.03 <0.01 <0.01 <0.01 0.03 >0.05<0.01 refractive index Viscosity (Pa · s) >200 >200 3-60 >200 >200 >200<1 Spreading X X ◯ X X X Δ Comparative Comparative ComparativeComparative Ingredient (wt %) Example 3 Example 4 Example 5 Example 6Acyl-group-containing composition of Example 7 Acyl-group-containingcomposition of Example 8 Sodium 11  4 lauraylglutamate Sodium lauryl 13diphenyl ether disulfonate Polyoxyethylene (5) 12 lauryl ether Glycerol17 17 17 20 Diglycerol Sorbitol POE (20) methyl glycoside SucrosePurified water 14 10 12  5 Liquid paraffin Isopropyl myristateIsostearyl isostearate Grape seed oil TEG + Silicone (10CS) Squarane 69Olive oil 58 58 63 Silicone (10CS) Glyceryltri-2- ethylhexanoicacidLow-boiling point silicone Stability X X X X Appearance separatedseparated separated separated Afterfeel X X X X Difference in — — — —refractive index Viscosity (Pa · s) — — — — Spreading — — — —

EXAMPLES 23-24

The gelatinous composition produced in Example 21 was stirred at 70° C.,the oil phase portion was added to the composition while stirring at 70°C., the remaining water phase portion was added to 100 parts by weightin all, and the mixture was cooled to produce a formulation. Thestability and afterfeel were evaluated. The results are shown in Table3. The compositions in Table 3 are shown in terms of % by weight.

COMPARATIVE EXAMPLE 7

The oil phase portion and the water phase portion shown in ComparativeExample 7 in Table 3 were respectively heated to 70° C. and dissolved,then the oil phase portion was mixed and emulsified with the water phaseportion, and the mixture was cooled to yield a formulation. Thestability and afterfeel were evaluated for the formulation. The resultsare shown in Table 3. The formulation composition in Table 3 is shown interms of % by weight. TABLE 3 Example 23 Example 24 Lotion Cream (Oilgel) Squarane 13 13 Composition of Example 7 1 1 Glycerol 6 6 (Oilphase) Stearic acid 2 3 Cetanol 1.5 5 Vaseline 5 Glyceryl tri-2- 4ethylhexanoate (Water phase) Triethanolamine 0.5 1 Citric acid SuitableSuitable amount amount Purified water rest rest Stability ◯ ◯ Afterfeel◯ ◯ Comparative Example 7 Cream (Oil phase) Squarane 13 Stearic acid 2Cetanol 1.5 Vaseline 5 Glyceryl tri-2- 4 ethylhexanoate (Water phase)Triethanolamine 0.5 Citric acid Suitable amount Composition of 0.05Production Example 1 Glycerol 6 Purified water rest Stability XAfterfeel X

REFERENCE EXAMPLE 1

The moisture absorption rate under high humidity and the moistureretention rate under low humidity were evaluated for the compositionproduced in Example 7 and urea as a contrast. Specifically, 1 g of driedsample was dried in a weighing bottle and weighed precisely, and leftstand in a desiccator under relative humidity as high as 84% at 25° C.while measuring the sample weight with time until 313 hours has elapsed.Then, the same sample was transferred into a desiccator under relativehumidity as low as 33% at 25° C., and left stand in the desiccator whilemeasuring the sample weight with time in the same manner as aboveconsidering the point 313 hours has elapsed as a test starting point (0hr). The moisture absorption rate was obtained in accordance with thefollowing equation. Moisture absorption rate (%)=(Wt —WO/WO)×100 WO: dryweight before being left stand, Wt: weight at the time of each measuring

The results are shown in Table 4. Urea showed its deliquescentproperties during the course of moisture absorption, but once it wasleft stand under low humidity, it released almost all its moisture. Onthe other hand, the acyl group-containing composition produced inExample 7 did not have deliquescent properties and showed high moistureretention compared with urea. TABLE 4 Moisture absorption rates underhigh humidity after different elapsed time (%) Sample 5 Hr 27 Hr 48 Hr120 Hr 197 Hr 313 Hr Composition 7.9 26.8 35.0 43.1 44.2 44.7 of Example7 Urea 0.2 3.2 7.4 24.7 42.6 72.7 Moisture absorption rates under lowhumidity after different elapsed time (%) Sample 0 Hr 25 Hr 49 Hr 75 Hr141 Hr Composition 44.7 22.3 10.9 7.8 7.0 of Example 7 Urea 72.7 1.2 0.30.4 0.3

EXAMPLES 25 TO 26, COMPARATIVE EXAMPLE 8

A skin lotion was prepared using the acyl group-containing compositionproduced in Example 7 so that it has a composition shown in Table 5 andevaluation was conducted for the skin lotion. The results are shown inTable 5. The composition in Table is shown in terms of % by weight.

The skin lotion prepared using the acyl group-containing compositionproduced in Example 7 had an excellent afterfeel. TABLE 5 ComparativeExample 25 Example 26 Example 8 Composition of 0.5 1 0 Example 7 Urea 00 1 1,3-Butylene 5 2 2 glycol Oleyl alchol 0.1 0 0 Ethanol 5 10 10Purified water rest rest rest pH 6.5 6.5 6.5 afterfeel ◯ ◯ X

EXAMPLE 27

The composition produced in Example 7 was used as a dispersant. Thedispersant was added to 300 ml of purified water so that the solidcontent concentration was 0.01% by weight, fine-grained titanium oxide(ISHIHARA SANGYO KAISHA, LTD.; “TTO-55(A)”, trademark) as a pigment wasadded to the above solution so that the solid content concentration was1% by weight, and the mixed solution was stirred and dispersed for 2minutes with a homomixer at 10000 rpm and normal temperature. Thedispersion was left stand at 40° C. and the transmittance of thesupernatant at 300 nm was measured with time. The results are shown inTable 6.

Since the fine-grained titanium oxide exerts its ultraviolet rayscreening effect when being dispersed, smaller transmittancemeasurements indicate that the titanium oxide is neither aggregated norprecipitated, but stably dispersed. From this point of view, thecomposition of Example 27 has excellent dispersion stability.

COMPARATIVE EXAMPLES 9 TO 11

The transmittance of the supernatant at 300 nm was measured with time inthe same manner as Example 25 except that the dispersant used in Example27 was replaced by the following ones. The results are shown in Table 6.

-   -   Comparative Example 9; sodium lauroylglutamate    -   Comparative Example 10; polyethyleneglycol(20) monostearate

Comparative Example 11; polyoxyethylene(20) sorbitanmonolaurate TABLE 6Change in transmittance of supernatant with time (T %) Dispersant 0 Hr 5Hr 30 Hr 50 Hr 75 Hr 100 Hr 200 Hr Example 27 Composition of 1.4 1.3 1.21.3 1.2 0.9 0.8 Example 7 Comparative Sodium 1.4 83.2 98.6 100 100 100100 Example 9 lauroylglutamate Comparative Polyethylene 1.4 1.3 1.2 13.581.3 85.1 97.3 Example 10 glycol(20) monostearate ComparativePolyoxyethylene(20) 1.4 1.7 3.2 10.0 9.9 84.5 88.5 Example 11 sorbitanmonolaurate

EXAMPLE 28, COMPARATIVE EXAMPLES 12 TO 13

The transmittance of the supernatant was measured with time under thesame conditions as Example 27 except that activated carbon (TakedaChemical Industries, Ltd., trademark: “Shirasagi”) was used as a pigmentinstead of fine-grained titanium oxide, the dispersant used in Example27 was replaced by the following ones and the transmittance was measuredat 300 nm and at 660 nm. The results are shown in Table 7. Smallertransmittance measurements indicate that the activated carbon is neitheraggregated nor precipitated, but stably dispersed. From this point ofview, the composition of Example 7 has particularly excellent dispersionstability.

-   -   Example 28; composition of Example 7    -   Comparative Example 12; sodium lauroylglutamate    -   Comparative Example 13; polyethyleneglycol(20) monostearate

Comparative Example 14; polyoxyethylene(20) sorbitanmonolaurate TABLE 7Change in transmittance of supernatant with time (T %) Dispersant 0 Hr 5Hr 30 Hr 80 Hr 150 Hr Example 28 Composition of 0.6 0.6 0.6 0.7 0.8Example 7 Comparative Sodium 0.6 0.6 0.6 0.7 5.7 Example 12lauroylglutamate Comparative Polyethylene 0.6 0.6 2.8 3.6 24.7 Example13 glycol(20) monostearate Comparative Polyoxyethylene 0.6 0.6 1.1 4.423.0 Example 14 (20) sorbitan monolaurate

INDUSTRIAL APPLICABILITY

The acyl group-containing composition of this invention is an anionicsurfactant which is applicable to the field of cosmetics such ascleansing agents, quasi drugs and makeups. It is a surfactant whichshows surface activity at low concentrations, is less irritating to theskin and has moisture retention. The acyl group-containing compositionis applicable to: cosmetics that do not leave the skin feeling sticky,but provide a moist feeling to improve the skin moisturizing effect;gelatinous compositions that can have arbitrary hardness from thehardness of a paste to that of a solid; cleansing agents that have anexcellent afterfeel; and dispersants for pigments that have excellentdispersibility.

1. A method of producing an acyl group-containing composition comprisinga step of reacting a long chain N-acyl acidic amino acid anhydriderepresented by the following formula (1): [Formula 1]

wherein R¹CO represents a long chain acyl group derived from a saturatedor unsaturated fatty acid with 2 to 20 carbon atoms; R² is hydrogen or alower alkyl group with 1 to 3 carbon atoms which is optionallysubstituted with a hydroxyl or carboxyl group; j, k are independentlyany of 0, 1 and 2 and are not 0 at the same time, with one or morecompounds having, per molecule, m functional groups of one kind or moreselected from the group consisting of hydroxyl, amino and thiol groupsin an aqueous solvent and/or a mixed solvent of water and an organicsolvent, which is defined as reaction step, wherein the acylgroup-containing composition comprises at least one acyl compoundrepresented by the following general formula (2): [Formula 2]

herein R¹CO, R², and j, k each represent the same as those defined inthe above formula (1); n (n is an integer of 2 to 20, including 2 and20) Zs are bonding portions to which m (m≧n) functional groups of onekind or more selected from the group consisting of hydroxyl, amino andthiol groups substituted on X bind and which are selected independentlyfrom the group consisting of —O—, —NR³— (R³ is hydrogen, or an alkyl, analkenyl, an aryl or an alkylaryl group with 1 to 10 carbon atoms) and—S—; X is a spacer of a straight, branched or cyclic hydrocarbon chainof molecular weight of 1,000,000 or less which optionally hassubstituents other than hydroxyl, amino and thiol groups and contains ordoes not contain an aromatic hydrocarbon; n substituents represented bythe following general formula (3): [Formula 3]

wherein reference characters each represent the same as those defined inthe above formula (2), which are attached to X via Z are independent ofeach other; and Y represents a carboxyl group or the salt thereof. 2.The method according to claim 2, wherein in the general formula (2), Xis a spacer of a straight, branched or cyclic hydrocarbon chain with 1to 40 carbon atoms which optionally has substituents other thanhydroxyl, amino and thiol groups and contains or does not contain anaromatic hydrocarbon.
 3. The method according to claim 1 or 2, whereinin said reaction step, the molar ratio of the total of the functionalgroups contained in the one or more compounds having, per molecule, mfunctional groups of one kind or more selected from the group consistingof hydroxyl, amino and thiol groups to the long chain N-acyl acidicamino acid anhydride represented by the formula (1) is 0.5 to 1.4 andthe pH of the reaction solution is kept at 4 to 14 at the time ofreaction.
 4. The method according to any one of claims 1 to 3, furthercomprising, as step(s) carried out after said reaction step, either oneor both of (i) a step of separating the reaction solution derived fromsaid reaction step into two layers, an organic layer and a water layer,by adjusting the pH of the reaction solution to 1 to 6 using a mineralacid to obtain an organic layer which contains the acyl group-containingcomposition, which is defined as an acid-precipitation andlayer-separation step and (ii) a step of separating, at 35° C. to 80°C., the mixture of the acyl group-containing composition, which containswater-soluble impurities such as inorganic salts, and the medium, whichsubstantially contains water and tertiary butanol as main ingredients,into a water layer and an organic layer containing the acylgroup-containing composition to remove impurities in the acylgroup-containing composition, which is defined as a washing step.
 5. Themethod according to any one of claims 1 to 4, wherein after saidreaction step, or after said acid-precipitation and layer-separationstep or washing step, the organic solvent is distilled off from theorganic layer, which contains the acyl group-containing composition,using a spray evaporator in which a mixed solution is allowed to takethe form of a vapor-liquid mixed phase and is sprayed within theevaporator to evaporate the solvent.
 6. An acyl group-containingcomposition comprising at least one acyl compound represented by thefollowing formula (2): [Formula 2]

wherein R¹CO represents a long chain acyl group derived from a saturatedor unsaturated fatty acid with 2 to 20 carbon atoms; R² is hydrogen or alower alkyl group with 1 to 3 carbon atoms which is optionallysubstituted with a hydroxyl or carboxyl group; j, k are independentlyany of 0, 1 and 2 and are not 0 at the same time; n (n is an integer of2 to 20, including 2 and 20) Zs are bonding portions to which m (m≧n)functional groups of one kind or more selected from the group consistingof hydroxyl, amino and thiol groups substituted on X bind and which areselected independently from the group consisting of —O—, —NR³— (R³ ishydrogen, or an alkyl, an alkenyl, an aryl or an alkylaryl group with 1to 10 carbon atoms) and —S—; X is a spacer of a straight, branched orcyclic hydrocarbon chain of molecular weight of 1,000,000 or less whichoptionally has substituents other than hydroxyl, amino and thiol groupsand contains or does not contain an aromatic hydrocarbon; n substituentsrepresented by the following general formula (3): [Formula 3]

wherein reference characters each represent the same as those defined inthe above formula (2), which are attached to X via Z are independent ofeach other; and Y represents a carboxyl group or the salt thereof,wherein the content of the acyl compound in the composition is 70% byweight or more, the content of free fatty acid is 3% by weight or less,and the content of a compound whose molecular weight is smaller thanthat of the acyl compound by 18 is 5% or less in terms of its area ratioto the acyl compound which is obtained by the analysis of liquidchromatography using a detector at 205 nm.
 7. The composition accordingto claim 6, comprising 0.5 to 30% by weight of a long chain N-acylacidic amino acid or a salt thereof.
 8. The composition according toclaim 6 or 7, wherein in the general formula (2), X is a spacer of astraight, branched or cyclic hydrocarbon chain with 1 to 40 carbon atomswhich optionally has substituents other than hydroxyl, amino and thiolgroups and contains or does not contain an aromatic hydrocarbon.
 9. Thecomposition according to any one of claims 6 to 8, wherein in thegeneral formula (2), R¹CO is a long chain acyl group derived from asaturated or unsaturated fatty acid with 8 to 20 carbon atoms.
 10. Thecomposition according to any one of claims 6 to 9, wherein in thegeneral formula (2), X has at least one group independently selectedfrom the group consisting of carboxyl, sulfonic acid, sulfate ester andphosphate ester groups and the salts thereof.
 11. The compositionaccording to any one of claims 6 to 10, comprising 0.2 to 1.5 equivalentof basic substance, as a counter ion, per 1 equivalent of dissociatedgroups in said acyl group-containing compound.
 12. The compositionaccording to any one of claims 6 to 11, wherein the transmittances at430 nm and 550 nm are both 90% or more when said acyl group-containingcomposition is formed into an aqueous solution having a solids contentof 20% by weight and a pH of
 10. 13. The composition according to claim10 or 11, further comprising other surfactant(s).
 14. The compositionaccording to any one of claims 6 to 13, comprising at least one acylcompound represented by the general formula (2) which is producedthrough a step of reacting a long chain N-acyl acidic amino acidanhydride represented by the following formula (1): [Formula 1]

wherein reference characters represent the same as those defined above,with one or more compounds having, per molecule, m functional groups ofone kind or more selected from the group consisting of hydroxyl, aminoand thiol groups in water and/or a mixed solvent of water and an organicsolvent, which is defined as reaction step.
 15. The compositionaccording to claim 14, wherein the one or more compounds having, permolecule, m functional groups of one kind or more selected from thegroup consisting of hydroxyl, amino and thiol groups independently have,per molecule, at least one group, other than hydroxyl, amino and thiolgroups, selected from the group consisting of carboxyl, sulfonic acid,sulfate ester and phosphate ester groups and the salts thereof.
 16. Thecomposition according to claim 14 or 15, wherein the composition isproduced by carrying out, after said reaction step, either one or bothof (i) a step of separating the reaction solution derived from saidreaction step into two layers, an organic layer and a water layer, byadjusting the pH of the reaction solution to 1 to 6 using a mineral acidto obtain an organic layer containing the acyl group-containingcomposition, which is defined as an acid-precipitation andlayer-separation step and (ii) a step of separating, at 35° C. to 80°C., the mixture of the acyl group-containing composition, which containswater-soluble impurities such as inorganic salts, and the medium, whichsubstantially contains water and tertiary butanol as main ingredients,into a water layer and an organic layer containing the acylgroup-containing composition to remove impurities in the acylgroup-containing composition, which is defined as a washing step. 17.The composition according to any one of claims 14 to 16, wherein thecomposition is produced by distilling off the organic solvent, aftersaid reaction step, or after said acid-precipitation andlayer-separation step or washing step, from the organic layer whichcontains the acyl group-containing composition using a spray evaporatorin which a mixed solution is allowed to take the form of a vapor-liquidmixed phase and is sprayed within the evaporator to evaporate thesolvent.
 18. A composition in the form of a liquid, a solid, a gel, apaste or a mist, comprising one or more of the acyl group-comprisingcompositions according to any one of claims 6 to
 17. 19. A cosmeticcomposition in the form of a liquid, a solid, a gel, a paste or a mist,comprising one or more of the acyl group-containing compositionsaccording to any one of claims 6 to
 17. 20. The cosmetic compositionaccording to claim 19, further comprising one or more polyhydroxylcompounds.
 21. The cosmetic composition according to claim 20, whereinthe content of polyhydroxyl compounds in the above described cosmeticcomposition is 0.1 to 60% by weight and the weight ratio of the contentof the acyl group-containing compositions to the content of thepolyhydroxyl compounds in said cosmetic composition is 10/1 to 1/100.22. The cosmetic composition according to claim 20 or 21, furthercomprising one or more oil ingredients and being in the form of a gel.23. A gelatinous composition comprising one kind or more of the acylgroup-containings compositions according to any one of claims 6 to 17,one or more polyhydroxyl compounds and one or more oil ingredients,wherein the water content in the gelatinous composition is 50% by weightor less and the composition of the gelatinous composition is suchthat 1) the total amount of the acyl group-containing compositions is0.1 to 40% by weight, 2) the total amount of the polyhydroxyl compoundsis 1 to 60% by weight, and 3) the total amount of the oil ingredients is1 to 95% by weight.
 24. The gelatinous composition according to claim23, wherein the difference in refractive index at 20° C. between thewater layer containing the acyl group-containing composition(s), thepolyhydroxyl compound(s) and water, and the oil layer containing the oilingredients, in the gelatinous composition is ±0.05 or less.
 25. Thegelatinous composition according to claim 23 or 24, wherein itsviscosity at 25° C. is 1,000 to 200,000 mPa·s.
 26. Use of the gelatinouscomposition according to any one of claims 23 to 25 for cleansingagents.
 27. A cosmetic composition, prepared by emulsifying thegelatinous composition according to any one of claims 23 to
 25. 28. Adispersant composition which comprises one or more of the acylgroup-containing compositions according to any one of claims 6 to 17 andis in the form of a liquid, a solid, a gel, a paste or a mist.